Ammonium Chloride → HCID 118005907, compound

HRID 1484713Notes

Reaction equation

HRID 1484713 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)[CH:5]=[C:4]([CH3:15])[C:3]=1[C:16]1[N:17]=[C:18]([NH:21][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[S:19][CH:20]=1.[BH4-].[Na+].[NH4+].[Cl-]>CO>[OH:14][CH:11]1[CH2:12][CH2:13][N:8]([C:6]2[CH:5]=[C:4]([CH3:15])[C:3]([C:16]3[N:17]=[C:18]([NH:21][C:22](=[O:29])[C:23]4[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=4)[S:19][CH:20]=3)=[C:2]([CH3:1])[CH:7]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 118006102HCID 118006102, compound

Product 1

HCID 118005907HCID 118005907, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(4-(2,6-dimethyl-4-(4-oxopiperidin-1-yl)phenyl)thiazol-2-yl)isonicotinamide (33 mg, 0.081 mmol) in methanol (5 mL) was added NaBH4 (33 mg, 0.78 mmol). The mixture was stirred for 30 min at rt. Then saturated aqueous NH4Cl solution (2 mL) was added to quench the reaction. The mixture was extracted with EtOAc (5×2 mL). After removal of solvent, the residue was purified on a silica gel column (EtOAc) to provide N-(4-(4-(4-hydroxypiperidin-1-yl)-2,6-dimethylphenyl)thiazol-2-yl)isonicotinamide as yellow solid (29.8 mg, 90%). MS (ESI) m/z 409.2 (M+H+).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture was extracted with EtOAc (5×2 mL)
  4. customAfter removal of solvent
  5. customthe residue was purified on a silica gel column (EtOAc)

Sources & evidence

ORD record
ord-8d177b363b0144249e8c4d3cf8d7c133
Source dataset
uspto-grants-2016_08
Patent number
US09422275B2

Reaction notes

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