Water → HCID 58515946, compound

HRID 717836Notes

Reaction equation

HRID 717836 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]3[CH:20]=[N:21][CH:22]=[C:18]3[C:17]([Cl:23])=[CH:16][C:15]=2[C:24]([O:26]C)=[O:25])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]3[CH:20]=[N:21][CH:22]=[C:18]3[C:17]([Cl:23])=[CH:16][C:15]=2[C:24]([OH:26])=[O:25])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 58515977HCID 58515977, compound

Product 1

HCID 58515946HCID 58515946, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 5-[4-(tert-butoxycarbonyl)piperazin-1-yl]-8-chloroimidazo[1,5-a]pyridine-6-carboxylate (120 mg, 0.3123 mmol) was stirred in methanol (2 mL) and 3.0 M sodium hydroxide in water (0.4 mL, 1.0 mmol) was added. The mixture was stirred at room temperature overnight. Acidification with a few drops of 1 M HCl (checked with litmus paper pH 6), evaporation and trituration with water gave the desired compound (94 mg, 79%). LCMS calculated for C17H22ClN4O4 (M+H)+: m/z=381.1. found: 380.9.

Workup

  1. customAcidification with a few drops of 1 M HCl (checked with litmus paper pH 6), evaporation and trituration with water

Sources & evidence

ORD record
ord-170205ceacf94fddb20b6f546bb86ba0
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

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