Water → HCID 57942414, compound

HRID 1898215Notes

Reaction equation

HRID 1898215 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:13]([C:19]([N:21]3[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]3)=[O:20])=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:28]([F:31])([F:30])[F:29].[BH4-].[Na+].O>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:13]([C:19]([N:21]3[CH2:22][CH2:23][CH:24]([OH:27])[CH2:25][CH2:26]3)=[O:20])=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=2)(=[O:9])=[O:10])=[CH:4][C:3]=1[C:28]([F:31])([F:29])[F:30]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 57942176HCID 57942176, compound

Product 1

HCID 57942414HCID 57942414, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-chloro-N-[5-chloro-2-(4-oxo-piperidine-1-carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide (20 mg), sodium borohydride (10 mg) in 1 mL of methanol was stirred at room temperature overnight. To the mixture was added water and the resulting mixture was extracted with ethyl acetate three times. The organic layer was washed with brine and dried. After the removal of solvents the residue was further purified by flash column (50% ethyl acetate in hexane) to afford the title compound as a white solid: 1H NMR: (CDCl3, ppm) δ 8.12 (d, 1H), 8.09 (d, 1H), 7.95 (dd, 1H), 7.80 (d, 1H), 7.62 (d, 1H), 4.05 (m, 1H), 3.88 (m, 1H), 3.47 (m, 1H), 3.36 (m, 1H), 3.02 (m, 1H), 1.94 (m, 1H), 1.73 (m, 1H), 1.58 (m, 1H), 1.48 (m, 2H); MS: (M+H)/z=498.0.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate three times
  2. washThe organic layer was washed with brine
  3. customdried
  4. customAfter the removal of solvents the residue
  5. customwas further purified by flash column (50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-8ba27bf37155439a9a523410b24ffecf
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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