2-Propanol, reaction products with ammonia, distn. residues → 1-Bromo-3-(3-(trifluoro methyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-7-yl)imidazo[1,5-a]pyrazin-8-amine

HRID 62479Notes

Reaction equation

HRID 62479 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH:12]2[CH2:17][CH2:16][N:15]3[C:18]([C:21]([F:24])([F:23])[F:22])=[N:19][N:20]=[C:14]3[CH2:13]2)[N:5]2[CH:10]=[CH:9][N:8]=[C:7](Cl)[C:6]=12.[NH3:25].CC(O)C>>[Br:1][C:2]1[N:3]=[C:4]([CH:12]2[CH2:17][CH2:16][N:15]3[C:18]([C:21]([F:24])([F:23])[F:22])=[N:19][N:20]=[C:14]3[CH2:13]2)[N:5]2[CH:10]=[CH:9][N:8]=[C:7]([NH2:25])[C:6]=12

Participants

3

Reactant 2

HCID 183319422-Propanol, reaction products with ammonia, distn. residuesHCID 903039897-(1-Bromo-8-chloroimidazo[1,5-a]pyrazin-3-yl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 903041061-Bromo-3-(3-(trifluoro methyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-7-yl)imidazo[1,5-a]pyrazin-8-amineYield 99%

Procedure

A solution of 7-(1-bromo-8-chloroimidazo[1,5-a]pyrazin-3-yl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine (335 mg, 0.978 mmol) in NH3-iPrOH (50 mL) was heated at 100° C. for 24 hours in a sealed tube. The reaction was completed by LC-MS, then cooled to room temperature. Remove the solvent in vacuo to give 1-bromo-3-(3-(trifluoro methyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-7-yl)imidazo[1,5-a]pyrazin-8-amine as a yellow solid (0.39 g, yield 99%).

Workup

  1. customRemove the solvent in vacuo

Sources & evidence

ORD record
ord-07c2a40c53a544cebbcbf5d1f64542d1
Source dataset
uspto-grants-2016_09
Patent number
US09446130B2

Reaction notes

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