tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate
Uses- Product Name
- tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate
- CAS No.
- 365996-06-1
- Chemical Name
- tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate
- Synonyms
- tert-butyl 2-broMo-6;5-Boc-2-bromo-6,7-dihydro-4H-thiazolo[5,4-c]pyridine;tert-Butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H);tert-butyl 2-bromo-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-...;tert-Butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridin-5(4H)-carboxylate;2-Bromo-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine, N-BOC protected;tert-butyl 2-broMo-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-carboxylate;tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate;tert-butyl 2-broMo-4H,5H,6H,7H-[1,3]thiazolo[5,4- c]pyridine-5-carboxylate;tert-butyl 2-bromo-6,7-dihydro-4H-[1,3]thiazolo[5,4-c]pyridine-5-carboxylate
- CBNumber
- CB01856206
- Molecular Formula
- C11H15BrN2O2S
- Formula Weight
- 319.22
- MOL File
- 365996-06-1.mol
tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate Property
- Melting point:
- 42-44 °C(Solv: ethyl ether (60-29-7))
- Boiling point:
- 390.9±42.0 °C(Predicted)
- Density
- 1.495±0.06 g/cm3(Predicted)
- storage temp.
- under inert gas (nitrogen or Argon) at 2-8°C
- pka
- 1.23±0.20(Predicted)
- Appearance
- White to off-white Solid
- InChI
- InChI=1S/C11H15BrN2O2S/c1-11(2,3)16-10(15)14-5-4-7-8(6-14)17-9(12)13-7/h4-6H2,1-3H3
- InChIKey
- RXXKNZKFRAFFOH-UHFFFAOYSA-N
- SMILES
- C1N(C(OC(C)(C)C)=O)CCC2N=C(Br)SC1=2
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- B694430
- Product name
- 2-Bromo-5-(tert-butoxycarbonyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine
- Packaging
- 1g
- Price
- $390
- Updated
- 2021/12/16
- Product number
- FB148706
- Product name
- tert-Butyl2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate
- Packaging
- 250mg
- Price
- $420
- Updated
- 2021/12/16
- Product number
- 8H51-9-02
- Product name
- 2-Bromo-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine, N-Boc protected
- Packaging
- 5G
- Price
- $432
- Updated
- 2021/12/16
- Product number
- HCH0122626
- Product name
- TERT-BUTYL-2-BROMO-6,7-DIHYDROTHIAZOLO[5,4-C]PYRIDINE-5(4H)CARBOXYLATE
- Purity
- 95.00%
- Packaging
- 0.5G
- Price
- $682
- Updated
- 2021/12/16
- Product number
- FB148706
- Product name
- tert-Butyl2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate
- Packaging
- 500mg
- Price
- $730
- Updated
- 2021/12/16
tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate Chemical Properties,Usage,Production
Uses
2-Bromo-5-(tert-butoxycarbonyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine is a reagent used for the synthesis of tetrahydrothiazolopyridines, which are potent antagonists for the smoothened (smo) receptor.
Uses
2-Bromo-5-(tert-butoxycarbonyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine is a reagent used for the synthesis of tetrahydrothiazolopyridines, which are potent antagonists for the smoothened (smo) receptor.
Synthesis
365996-05-0
365996-06-1
Method G - Step e: Synthesis of tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate [0134] To a 100 mL DMF solution containing isoamyl nitrite (8.8 mL, 62.8 mmol) and copper(II) bromide (10.7 g, 48 mmol) was added tert-butyl 2-amino-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate (10 g, 39.2 mmol) at 0°C. The reaction was carried out at 40°C and the reaction mixture was purified. The reaction mixture was stirred at 40°C for 30 min and then concentrated by evaporation. The concentrate was dissolved in 50 mL of water and extracted with dichloromethane (100 mL × 2). The organic phases were combined, washed with brine (30 mL × 2), and dried over anhydrous sodium sulfate. Purification by silica gel column chromatography (eluent: dichloromethane) afforded the target product tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate (5.3 g, 42.4%) as a yellow solid.
References
[1] Heterocycles, 2004, vol. 63, # 7, p. 1555 - 1561
[2] Patent: WO2014/113191, 2014, A1. Location in patent: Paragraph 0133; 0134
[3] Patent: US2013/144061, 2013, A1. Location in patent: Paragraph 0244; 0245; 0246; 0247
[4] Journal of Medicinal Chemistry, 2014, vol. 57, # 9, p. 3687 - 3706
[5] Patent: WO2018/13774, 2018, A1. Location in patent: Page/Page column 309
tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate Preparation Products And Raw materials
Raw materials
Preparation Products
tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate Suppliers
- Tel
- --
- Fax
- --
- sales@carbosynth.com
- Country
- United Kingdom
- ProdList
- 6005
- Advantage
- 58
- Tel
- --
- Fax
- --
- enquiries@keyorganics.net
- Country
- United Kingdom
- ProdList
- 851
- Advantage
- 58
- Tel
- --
- Fax
- --
- info@manchesterorganics.com
- Country
- United Kingdom
- ProdList
- 6834
- Advantage
- 67
- Tel
- --
- Fax
- --
- sales@apolloscientific.co.uk
- Country
- United Kingdom
- ProdList
- 6084
- Advantage
- 88
View Lastest Price from tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate manufacturers
- Product
- tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate 365996-06-1
- Price
- US $5.50/KG
- Min. Order
- 1KG
- Purity
- 98%-99%
- Supply Ability
- 1kg-100kg
- Release date
- 2020-01-07