Application
ChemicalBook > CAS DataBase List > 2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-(6-broMo-1H-benziMidazol-2-yl)-, 1,1-diMethylethyl ester,(1R,3S,4S)-

2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-(6-broMo-1H-benziMidazol-2-yl)-, 1,1-diMethylethyl ester,(1R,3S,4S)-

Application
Product Name
2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-(6-broMo-1H-benziMidazol-2-yl)-, 1,1-diMethylethyl ester,(1R,3S,4S)-
CAS No.
1256387-74-2
Chemical Name
2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-(6-broMo-1H-benziMidazol-2-yl)-, 1,1-diMethylethyl ester,(1R,3S,4S)-
Synonyms
PLD-74-2;Dipavir intermediate;Ledipasvir Impurity 8;Ledipasvir side chain 2;Ledipasvir interMediates;Ledipasvir Intermediate 06;Benzenesulfonicacid,4-methyl-,3-methylpropylester;(1R,3S,4S)-3-(6-Bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2...;(1R,3S,4S)-2-Boc-3-(6-bromo-2-benzimidazolyl)-2-azabicyclo[2.2.1]heptane;(IR,35,4S)-3-(6-Bromo-IH-benzimidazol-2-yl)-2-azabicyclo[2.2.1lheptane-2-c
CBNumber
CB42715988
Molecular Formula
C18H22BrN3O2
Formula Weight
392.29
MOL File
1256387-74-2.mol
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2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-(6-broMo-1H-benziMidazol-2-yl)-, 1,1-diMethylethyl ester,(1R,3S,4S)- Property

Boiling point:
554.3±30.0 °C(Predicted)
Density 
1.455±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
pka
10.68±0.10(Predicted)
Appearance
White to yellow Solid
InChI
InChI=1S/C18H22BrN3O2/c1-18(2,3)24-17(23)22-12-6-4-10(8-12)15(22)16-20-13-7-5-11(19)9-14(13)21-16/h5,7,9-10,12,15H,4,6,8H2,1-3H3,(H,20,21)/t10-,12+,15-/m0/s1
InChIKey
IODPTNKFQCJTSI-NVBFEUDRSA-N
SMILES
[C@]12([H])C[C@]([H])(CC1)[C@@H](C1NC3=CC(Br)=CC=C3N=1)N2C(OC(C)(C)C)=O
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P330Rinse mouth.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

AK Scientific
Product number
9852BB
Product name
(1R,3S,4S)-Tert-butyl3-(6-bromo-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate
Packaging
1g
Price
$232
Updated
2021/12/16
AK Scientific
Product number
9852BB
Product name
(1R,3S,4S)-Tert-butyl3-(6-bromo-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate
Packaging
5g
Price
$546
Updated
2021/12/16
Ambeed
Product number
A279141
Product name
(1R,3S,4S)-tert-Butyl3-(6-bromo-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate
Purity
95%
Packaging
250mg
Price
$37
Updated
2021/12/16
Ambeed
Product number
A279141
Product name
(1R,3S,4S)-tert-Butyl3-(6-bromo-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate
Purity
95%
Packaging
1g
Price
$78
Updated
2021/12/16
Crysdot
Product number
CD11314404
Product name
(1R,3S,4S)-tert-Butyl3-(6-bromo-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate
Purity
97%
Packaging
1g
Price
$99
Updated
2021/12/16
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2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-(6-broMo-1H-benziMidazol-2-yl)-, 1,1-diMethylethyl ester,(1R,3S,4S)- Chemical Properties,Usage,Production

Application

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester can be used as a pharmaceutical synthesis intermediate, such as Harvoni, a combination of the novel antiviral NS5A inhibitor Letipasvir (GS5885) and the NS5B blocker Sofosbuvir, which is a blockbuster hepatitis C treatment drug approved by Gilead in December 2013.

Synthesis

1256387-73-1

1256387-74-2

General procedure for the synthesis of tert-butyl (1R,3S,4S)-3-[(2-amino-4-bromophenyl)carbamoyl]methyl-2-azabicyclo[2.2.1]heptane-2-carboxylate from (1R,3S,4S)-3-(6-bromo-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate: 1. 3-[(2-amino-4-bromophenyl)carbamoyl]-2-azabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (617) was dissolved in ethanol, placed in a sealed tube and heated at 130 °C overnight, then warmed to 170 °C and continued to heat for 3 days. The reaction was monitored by LC-MS, showing the generation of a mixture of the target product and the Boc protecting group cleavage product (in a ratio of about 1:1). 2. Upon completion of the reaction, the reaction mixture was concentrated and then dissolved in hydrochloric acid. 3. di-tert-butyl dicarbonate (0.6 eq.) was added to the solution and the reaction mixture was stirred overnight at room temperature. 4. The reaction mixture was concentrated and purified by fast column chromatography (silica gel as stationary phase, eluent 20% to 80% ethyl acetate/hexane gradient) to afford the target product (1R,3S,4S)-tert-butyl 3-(6-bromo-1H-benzo[d]imidazol-2-yl)-2- azabicyclo[2.2.1]heptane-2- carboxylate (618, 0.383 g, yield 72%) as an orange foamy solid.

References

[1] Patent: WO2013/40492, 2013, A2. Location in patent: Page/Page column 91
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 5, p. 2033 - 2046

2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-(6-broMo-1H-benziMidazol-2-yl)-, 1,1-diMethylethyl ester,(1R,3S,4S)- Preparation Products And Raw materials

Raw materials

Preparation Products

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2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-(6-broMo-1H-benziMidazol-2-yl)-, 1,1-diMethylethyl ester,(1R,3S,4S)- Suppliers

China 165 India 2 United States 1 Global 168
Standardpharm Co. Ltd.
Tel
86-714-3992388
Email
overseasales1@yongstandards.com
Country
United States
ProdList
14332
Advantage
58
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View Lastest Price from 2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-(6-broMo-1H-benziMidazol-2-yl)-, 1,1-diMethylethyl ester,(1R,3S,4S)- manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
Ledipasvir interMediates;(1R,3S,4S)-tert-butyl 3-(6-broMo-1Hbenzo[d]iMidazol-2-yl)-2-azabicyclo[2,2,1] heptanes-2-carboxylate 1256387-74-2
Price
US $0.00-0.00/KG
Min. Order
5g
Purity
99%+
Supply Ability
100 tons
Release date
2019-12-25
Career Henan Chemical Co
Product
2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-(6-broMo-1H-benziMidazol-2-yl)-, 1,1-diMethylethyl ester,(1R,3S,4S)- 1256387-74-2
Price
US $1.00/kg
Min. Order
1kg
Purity
95%-99%
Supply Ability
100kg
Release date
2018-12-19

1256387-74-2, 2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-(6-broMo-1H-benziMidazol-2-yl)-, 1,1-diMethylethyl ester,(1R,3S,4S)-Related Search:

(S)-Amlodipine (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate (1S)-1-(diphenylphosphino)-2-[(1R)-1-(diphenylphosphino)ethyl]-Ferrocene (S)-1-[(R)-2-(DI-TERT.-BUTYLPHOSPHINO)FERROCENYL]ETHYLBIS(2-METHYLPHENYL)PHOSPHI (1R,2R)-(-)-1,2-Diaminocyclohexane (1S)-4,5-Dimethoxy-1-[(methylamino)methyl]benzocyclobutane hydrochloride Ledipasvir ledipasvir interMediate ledipasvir interMediate 2,7-DibroMo-9,9-difluoro-9H-fluorene (S)-2-((Methoxycarbonyl)aMino)-3-Methylbutanoic acid 2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-(6-broMo-1H-benziMidazol-2-yl)-, 1,1-diMethylethyl ester,(1R,3S,4S)- (S)-5-BOC-5-AZASPIRO[2.4]HEPTANE-6-CARBOXYLIC ACID 1-(7-broMo-9,9-difluoro-9H-fluoren-2-yl)-2-chloro-Ethanone ledipasvir interMediate (3S)-N-Boc-2-azabicyclo[2.2.1]heptane-3-carboxylic acid

  • 2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-(6-broMo-1H-benziMidazol-2-yl)-, 1,1-diMethylethyl ester,(1R,3S,4S)-
  • (1R,3S,4S)-3-(6-Bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
  • (1R,3S,4S)-tert-butyl 3-(6-broMo-1H-benzo[d]iMidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate
  • (1R,3S,4S)-tert-butyl 3-(6-broMo-1Hbenzo[d]iMidazol-2-yl)-2-azabicyclo[2,2,1] heptanes-2-carboxylate
  • Ledipasvir interMediates
  • (1R,3S,4S)-3-(6-Bromo-1Hbenzimidazol-2-yl)-2-azabicyclo[2,2,1]heptane--2-carboxylic acid-1,1-dimethylethyleste
  • Ledipasvir side chain 2
  • tert-butyl (1R,3S,4S)-3-(6-bromo-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate
  • Ledipasvir Intermediate 06
  • (1R,3S4S)-3(6-Bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1] heptane-2-carboxylic acid 1,1-dimehylethyl ester
  • (IR,35,4S)-3-(6-Bromo-IH-benzimidazol-2-yl)-2-azabicyclo[2.2.1lheptane-2-c
  • (1R,3S,4S)-tert-butyl 3-(6-broMo-1H-benzo[d]iMidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate1256387-74-2
  • Ledipasvir Impurity 8
  • tert-butyl (1S,2S,4R)-2-(6-bromo-1H-benzimidazol-2-yl)-3-azabicyclo[2.2.1]heptane-3-carboxylate
  • tert-butyl(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate
  • 2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-(6-broMo-1H-benziMidazol-2-yl)-, 1,1-diMethylethyl ester,(1R,3S,4S)- ISO 9001：2015 REACH
  • 2-Azabicyclo[2.2.1]heptane-2-carboxylicacid,3-(6-broMChemicalbooko-1H-benziMidazol-2-yl)-,1,1-diMethylethylester,(1R,3S,4S)-
  • (1R,3S,4S)-3-(6-Bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2...
  • Dipavir intermediate
  • Benzenesulfonicacid,4-methyl-,3-methylpropylester
  • Carbamicacid,[(1S,3R)-3-(aminomethyl)cyclop entyl]-,1,1-dimethylethylester(13CI)
  • 2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-(6-broMo-1H-benziMidazol-2-yl)-, 1,1-diMethylethyl ester,(1R,3S,4S)- 1
  • PLD-74-2
  • tert-butyl (1R,3S,4S)-3-(5-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate
  • (1R,3S,4S)-2-Boc-3-(6-bromo-2-benzimidazolyl)-2-azabicyclo[2.2.1]heptane
  • tert-Butyl 3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate
  • 1256387-74-2