Water → HCID 19972899, compound

HRID 1451927Notes

Reaction equation

HRID 1451927 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([C:10]3([C:17](=[S:20])[NH:18][CH3:19])[CH2:15][CH2:14][CH2:13][CH2:12][C:11]3=[O:16])=[CH:6][N:5]2[CH:21]=1.[BH4-].[Na+].O>CO>[OH:16][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][C:10]1([C:7]1[CH:8]=[CH:9][C:4]2[N:5]([CH:21]=[C:2]([CH3:1])[N:3]=2)[CH:6]=1)[C:17](=[S:20])[NH:18][CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 19972896N-Methyl-1-(2-methylimidazo[1,2-a]pyridin-6-yl)-2-oxocyclohexanecarbothioamide

Product 1

HCID 19972899HCID 19972899, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.03 g of 1-(2-methylimidazo[1,2-a ]pyridin-6-yl)-N-methyl-2-oxocyclohexanecarbothioamide was suspended in 30 ml of methanol. The obtained suspension was cooled with ice, followed by the addition of 0.15 g of sodium borohydride. The obtained mixture was stirred for one hour, followed by the addition of 50 ml of water. The insoluble matter was recovered by filtration and recrystallized from ethanol and then from acetonitrile to give 1.24 g of the title compound (white powder) as a single diastereomer (yield: 41%).

Workup

  1. temperatureThe obtained suspension was cooled with ice
  2. filtrationThe insoluble matter was recovered by filtration
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-808f26e9213b4a4c8a95d523e0ffc932
Source dataset
uspto-grants-1997_02
Patent number
US05605907

Reaction notes

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