Dichloromethane → N-(2-bromo-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1-methyl-4-(6-methylpyridin-2-yl)-1H-pyrazole-5-carboxamide

HRID 60151Notes

Reaction equation

HRID 60151 reaction equation
Cl.[Br:2][C:3]1[N:12]=[C:6]2[CH2:7][CH:8]([NH2:11])[CH2:9][CH2:10][N:5]2[N:4]=1.C(Cl)Cl.[CH3:16][N:17]1[C:21]([C:22](Cl)=[O:23])=[C:20]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[N:26]=2)[CH:19]=[N:18]1.C(=O)([O-])O.[Na+]>C(N(CC)CC)C>[Br:2][C:3]1[N:12]=[C:6]2[CH2:7][CH:8]([NH:11][C:22]([C:21]3[N:17]([CH3:16])[N:18]=[CH:19][C:20]=3[C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[N:26]=3)=[O:23])[CH2:9][CH2:10][N:5]2[N:4]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 903834571-methyl-4-(6-methylpyridin-2-yl)-1H-pyrazole-5-carbonyl chlorideHCID 1177612012-Bromo-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-7-amine hydrochloride

Product 1

HCID 90383444N-(2-bromo-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1-methyl-4-(6-methylpyridin-2-yl)-1H-pyrazole-5-carboxamideYield 46.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The 2-bromo-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-7-amine hydrochloride (38 mg) obtained in (Example 5.16) <Step 6> was added at 0° C. to a methylene chloride (1 ml) solution of the 1-methyl-4-(6-methylpyridin-2-yl)-1H-pyrazole-5-carbonyl chloride (35 mg) obtained in (Example 5.47) <Step 1> and triethylamine (0.06 ml). The obtained mixture was stirred for 30 minutes. Thereafter, a saturated sodium hydrogen carbonate aqueous solution (2 ml) was added to the reaction solution, and the mixed solution was then purified by LC/MS, so as to obtain the title compound (29 mg) in the form of a white solid.

Workup

  1. customthe mixed solution was then purified by LC/MS

Sources & evidence

ORD record
ord-3021236a46484a16af24bc003e227901
Source dataset
uspto-grants-2016_09
Patent number
US09440970B2

Reaction notes

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