Water → HCID 18998669, compound

HRID 1451928Notes

Reaction equation

HRID 1451928 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][C:8]([C:11]3([C:18](=[S:21])[NH:19][CH3:20])[CH2:16][CH2:15][CH2:14][CH2:13][C:12]3=[O:17])=[CH:7][N:6]2[CH:22]=1.[BH4-].[Na+].O>CO>[OH:17][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][C:11]1([C:8]1[CH:9]=[CH:10][C:5]2[N:6]([CH:22]=[C:3]([C:2]([F:24])([F:23])[F:1])[N:4]=2)[CH:7]=1)[C:18](=[S:21])[NH:19][CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 19972900HCID 19972900, compound

Product 1

HCID 18998669HCID 18998669, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.86 g of 1-(2-trifluoromethylimidazo-[1,2-a ]pyridin-6-yl)-N-methyl-2-oxocyclohexanecarbothioamide was suspended in 17 ml of methanol. The obtained suspension was cooled with ice, followed by the addition of 0.08 g of sodium borohydride. The obtained mixture was stirred for one hour, followed by the addition of water. The resulting mixture was extracted with chloroform. The organic phase was dried over anhydrous magnesium sulfate and freed from the solvent by distillation. The obtained solid was recrystallized from ethyl acetate/n-hexane to give 1.53 g of the title compound as a white solid (yield: 84%).

Workup

  1. temperatureThe obtained suspension was cooled with ice
  2. extractionThe resulting mixture was extracted with chloroform
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. distillationfreed from the solvent by distillation
  5. customThe obtained solid was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-005486b19ee045c5b5dbc0e540214a6e
Source dataset
uspto-grants-1997_02
Patent number
US05605907

Reaction notes

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