Sodium borohydride → HCID 67439041, compound

HRID 2089446Notes

Reaction equation

HRID 2089446 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[S:10][C:11]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[C:12]([C:14](=[O:29])[NH:15][C:16]2[CH:17]=[N:18][N:19]([CH3:28])[C:20]=2[CH:21]2[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]2)[N:13]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[S:10][C:11]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[C:12]([C:14](=[O:29])[NH:15][C:16]2[CH:17]=[N:18][N:19]([CH3:28])[C:20]=2[CH:21]2[CH2:22][CH2:23][CH:24]([OH:27])[CH2:25][CH2:26]2)[N:13]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58464861HCID 58464861, compound

Product 1

HCID 67439041HCID 67439041, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl 2-(2,6-difluorophenyl)-4-(1-methyl-5-(4-oxocyclohexyl)-1H-pyrazol-4-ylcarbamoyl)thiazol-5-ylcarbamate (68 mg, 0.13 mmol) was dissolved in methanol (3 mL) and sodium borohydride (16 mg, 0.39 mmol) was added. The mixture was stirred at RT for 30 min then quenched with sat. NaHCO3 and extracted with ethyl acetate three times. Combined organic layers were dried over sodium sulfate, filtered and concentrated to give the crude tert-butyl 2-(2,6-difluorophenyl)-4-(5-(4-hydroxycyclohexyl)-1-methyl-1H-pyrazol-4-ylcarbamoyl)thiazol-5-ylcarbamate (58 mg, 85%).

Workup

  1. customthen quenched with sat. NaHCO3
  2. extractionextracted with ethyl acetate three times
  3. dry with materialCombined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-578fef0a72b54071b56427ab2a2cc431
Source dataset
uspto-grants-2013_05
Patent number
US08436001B2

Reaction notes

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