m-Chloroperbenzoic acid → HCID 178523532, compound

HRID 1093719Notes

Reaction equation

HRID 1093719 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[O:12]=[C:13]([N:29]1[CH2:34][CH2:33][CH:32]([S:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[C:42]([F:45])([F:44])[F:43])[CH2:31][CH2:30]1)[CH2:14][NH:15][C:16]([C:18]1[CH:22]=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[NH:20][N:19]=1)=[O:17]>C(Cl)Cl>[O:12]=[C:13]([N:29]1[CH2:30][CH2:31][CH:32]([S:35]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[C:42]([F:44])([F:43])[F:45])=[O:9])[CH2:33][CH2:34]1)[CH2:14][NH:15][C:16]([C:18]1[CH:22]=[C:21]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:20][N:19]=1)=[O:17]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178523530HCID 178523530, compound

Product 1

HCID 178523532HCID 178523532, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperbenzoic acid (18.5 mg, 0.1 mmol) was added to a cold (0-4° C.) solution of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-phenylsulfanyl)-piperidin-1-yl]-ethyl}-amide (50 mg, 0.1 mmol) in DCM (10 mL) and stirring was continued for 1 hr. The reaction mixture was concentrated. Purification by column chromatography (using 60-120 silica gel and 0.6% MeOH in CHCl3 as eluent) afforded 30 mg (58.35% yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzenesulfinyl)-piperidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 505.15, 95.9%. 1H NMR (300 MHz, DMSO-d6): δ 13.8 (s, 1H), 8.2-7.9 (m, 4H), 7.9-7.8 (m, 3H), 7.6-7.4 (t, 2H), 7.4 (t, 1H), 7.1 (s, 1H), 4.5 (d, 1H), 4.2 (d, 2H), 4.0 (d, 1H), 3.1 (m, 2H), 2.8-2.5 (m, 2H), 1.9 (d, 1H), 1.7 (dd, 1H), δ 1.6-1.4 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customPurification by column chromatography (using 60-120 silica gel and 0.6% MeOH in CHCl3 as eluent)

Sources & evidence

ORD record
ord-b23489f78bbe49acb5e574ad83538f96
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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