Name: 6-Bromo[1,2,4]triazolo[1,5-a]pyridine | 6-Bromo[1,2,4]triazolo[1,5-a]pyridine
Brand: Ambeed
SKU: A192440

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Dabigatran etexilate is the orally active prodrug of dabigatran and is a reversible and selective, direct thrombin inhibitor (DTI) with Ki value of 4.5 nM.

Synonyms: 6-Bromo[1,2,4]triazolo[1,5-a]pyridine

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Quality Control of 6-Bromo[1,2,4]triazolo[1,5-a]pyridine Purity: 98% SDS Specification

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NMR

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Product Details of 6-Bromo[1,2,4]triazolo[1,5-a]pyridine

CAS No. :	356560-80-0
Formula :	C₆H₄BrN₃
M.W :	198.02
SMILES Code :	BrC1=CN2C(C=C1)=NC=N2
Synonyms :	6-Bromo[1,2,4]triazolo[1,5-a]pyridine
MDL No. :	MFCD08689534
InChI Key :	CXRXKDSDRWLKTK-UHFFFAOYSA-N
Pubchem ID :	11513934

Safety of 6-Bromo[1,2,4]triazolo[1,5-a]pyridine

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of 6-Bromo[1,2,4]triazolo[1,5-a]pyridine

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 356560-80-0 ]
Downstream synthetic route of [ 356560-80-0 ]

[ 356560-80-0 ] Synthesis Path-Upstream 1~3

1
[ 138888-98-9 ]
[ 356560-80-0 ]

Yield	Reaction Conditions	Operation in experiment
72%	With pyridine; hydroxylamine-O-sulfonic acid In methanol at 0 - 20℃; for 12 h; Inert atmosphere	To a solution of N'-(5-bromo-pyridin-2-yl)-N,N-dimethyl-formamidine (4 g, 1 7.54 mmol, 1 .00 equiv) in methanol (40 mL) maintained under nitrogen at 0 °C was added pyridine (4 mL, 2,00 equiv) and (aminooxy)sulfonic acid (3 , 6 g, 31 .83 mmol, 1 .30 equiv). The resulting solution was stirred for 1 2 h at rt. After the reaction completed, the mixture was concentrated under vacuum The residue was diluted with 1 50 mL of ethyl acetate then washed with 1 x50 mL of saturated aqeous sodium carbonate solution and 2x50 mL of water. The organic layer was dried over anhydrous sodium sulfate then concentrated under vacuum. The residue was purified on a sil ica gel column eluted with ethyl acetate/hexane ( I ; 1 ) to give 2.5 g (72percent) title compound as a solid. LC/MS (Method D, ESI): RT= 1.1 min, m/z = 198.0 [M+H]
72%	With pyridine; hydroxylamine-O-sulfonic acid In methanol at 0 - 20℃; for 12 h; Inert atmosphere	To a solution of N'-(5- bromo-pyridin-2-yl)-N,N-dimethyl-formamidine (4 g, 1 7.54 mmol, 1 .00 equiv) in methanol (40 mL) maintained under nitrogen at 0 °C was added pyridine (4 mL, 2,00 equiv) and (aminooxy)sulfonic acid (3 , 6 g, 31 .83 mmol, 1 .30 equiv). The resulting solution was stirred for 1 2 h at rt. After the reaction completed, the mixture was concentrated under vacuum The residue was diluted with 1 50 mL of ethyl acetate then washed with 1 x50 mL of saturated aqeous sodium carbonate solution and 2x50 mL of water. The organic layer was dried over anhydrous sodium sulfate then concentrated under vacuum. The residue was purified on a sil ica gel column eluted with ethyl acetate/hexane ( I ; 1 ) to give 2.5 g (72percent) title compound as a solid. LC/MS (Method D, ESI): RT= 1 . 1 min, m z = 198.0 [M+H] ^"
72%	With pyridine; hydroxylamine-O-sulfonic acid In methanol at 0 - 20℃; for 12 h; Inert atmosphere	To a solution of N'-(5-bromo-pyridin-2-yl)-N,N-dimethyl-formamidine (4 g, 17.54 mmol, 1.00 equiv) in MeOH (40 mL) maintained under nitrogen at 0 °C was added pyridine (4 mL, 2.00 equiv) and (aminooxy)sulfonic acid (3.6 g, 31 .83 mmol, 1.30 equiv). The resulting solution was stirred for 12 h at rt. After the reaction completed, the mixture was concentrated under vacuum. The residue was diluted with 150 mL of ethyl acetate then washed with 1x50 mL of saturated aqeous sodium carbonate solution and 2x50 mL of water. The organic layer was dried over anhydrous sodium sulfate then concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/hexane (1 : 1 ) to give 2.5 g (72percent) title compound as a solid. LC/MS (Method D, ESI): RT= 1.15 min, m/z = 198.0 [M+H] ⁺.

72%	at 0 - 20℃; for 12 h; Inert atmosphere	[0206] Step 2. 6-Bromo-[1,2,4ltriazolo[1,5-alpyridine. To a solution of N’-(5-bromo- pyridin-2-yl)-N,N-dimethyl-formamidine (4 g, 17.54 mmol, 1.00 equiv) in methanol (40 mL) maintained under nitrogen at 0 °C was added pyridine (4 mL, 2.00 equiv) and (aminooxy)sulfonic acid (3.6 g, 31.83 mmol, 1.30 equiv). The resulting solution was stirred for 12 h at rt. After the reaction completed, the mixture was concentrated under vacuum. The residue was diluted with 150 mL of ethyl acetate then washed with 1x50 mL of saturated aqeous sodium carbonate solution and 2x50 mL of water. The organic layer was dried over anhydrous sodium sulfate then concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/hexane (1:1) to give 2.5 g (72percent) title compound as a solid. LC/MS (Method D, ESI): RT= 1.15 mi m/z = 198.0 [M+H].
72%	With pyridine; hydroxylamine-O-sulfonic acid In methanol at 0 - 20℃; for 12 h; Inert atmosphere	Step 2. 6-Bromo-rL2,41triazolorL5-alpyridine. To a solution of N'-(5-bromo- pyridin-2-yl)-N,N-dimethyl-formamidine (4 g, 17.54 mmol, 1.00 equiv) in methanol (40 mL) maintained under nitrogen at 0 °C was added pyridine (4 mL, 2.00 equiv) and (aminooxy) sulfonic acid (3.6 g, 31.83 mmol, 1.30 equiv). The resulting solution was stirred for 12 h at rt. After the reaction completed, the mixture was concentrated under vacuum. The residue was diluted with 150 mL of ethyl acetate then washed with 1x50 mL of saturated aqeous sodium carbonate solution and 2x50 mL of water. The organic layer was dried over anhydrous sodium sulfate then concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/hexane (1: 1) to give 2.5 g (72percent) title compound as a solid. LC/MS (Method D, ESI): RT= 1.15 min, m/z = 198.0 [M+H]⁺.

References: [1] Patent: WO2013/127266, 2013, A1, . Location in patent: Page/Page column 141.
[2] Patent: WO2013/127267, 2013, A1, . Location in patent: Page/Page column 92.
[3] Patent: WO2013/127268, 2013, A1, . Location in patent: Page/Page column 67.
[4] Patent: WO2013/130935, 2013, A1, . Location in patent: Paragraph 0206.
[5] Patent: WO2013/130943, 2013, A1, . Location in patent: Paragraph 0214.
[6] Patent: WO2004/43940, 2004, A1, . Location in patent: Page 84.
[7] Patent: WO2005/116029, 2005, A1, . Location in patent: Page/Page column 66.

2
[ 1075260-65-9 ]
[ 356560-80-0 ]

References: [1] Patent: WO2008/128953, 2008, A1, . Location in patent: Page/Page column 113-114.

3
[ 1072-97-5 ]
[ 356560-80-0 ]

References: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 12, p. 3614 - 3627.
[2] European Journal of Organic Chemistry, 2005, # 17, p. 3761 - 3765.
[3] Patent: WO2013/127266, 2013, A1, .
[4] Patent: WO2013/127267, 2013, A1, .
[5] Patent: WO2013/127268, 2013, A1, .
[6] Patent: WO2013/130935, 2013, A1, .
[7] Patent: WO2013/130943, 2013, A1, .
[8] Patent: WO2008/128953, 2008, A1, .
[9] Patent: WO2004/43940, 2004, A1, .
[10] Patent: WO2005/116029, 2005, A1, .
[11] Patent: KR2018/131662, 2018, A, .