m-Chloroperbenzoic acid → HCID 24985751, compound

HRID 544931Notes

Reaction equation

HRID 544931 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:27])=[C:11]([NH:13][C:14]([C:16]3[S:17][C:18]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)=[CH:19][CH:20]=3)=[O:15])[CH:12]=2)=[O:6])[CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:36])C=1>C(Cl)Cl>[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:27])=[C:11]([NH:13][C:14]([C:16]3[S:17][C:18]([C:21]4[CH:22]=[N+:23]([O-:36])[CH:24]=[CH:25][CH:26]=4)=[CH:19][CH:20]=3)=[O:15])[CH:12]=2)=[O:6])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59761399HCID 59761399, compound

Product 1

HCID 24985751HCID 24985751, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a slurry of N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-5-(pyridin-3-yl)thiophene-2-carboxamide (Example 149, 30 mg, 0.079 mmol) in CH2Cl2 (0.5 mL) at rt was added m-CPBA (19 mg, 0.083 mmol) and the resulting slurry was stirred at rt for 30 min then at 35° C. for 4.5 h. The mixture was concentrated under vacuum and the resulting solid was slurried in MeOH (˜2 mL) and the solid was collected by vacuum filtration and rinsed with add'n MeOH (˜1 mL). The resulting solid was dried in the funnel then under vacuum overnight to afford 25 mg (80%) of an off-white solid as the title compound (Example 196). HPLC Ret. Time=2.34 min, LCMS [M+H]+ 394.10.

Workup

  1. waitat 35° C. for 4.5 h
  2. concentrationThe mixture was concentrated under vacuum
  3. filtrationthe solid was collected by vacuum filtration
  4. washrinsed with add'n MeOH (˜1 mL)
  5. customThe resulting solid was dried in the funnel

Sources & evidence

ORD record
ord-ac14f0188eb94d7788d9ffbc6dccf739
Source dataset
uspto-grants-2011_05
Patent number
US07935696B2

Reaction notes

Loading…