m-Chloroperbenzoic acid → HCID 59786558, compound

HRID 1661457Notes

Reaction equation

HRID 1661457 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][C@H:18]([C:28]4[CH:33]=[CH:32][C:31]([S:34][CH3:35])=[CH:30][CH:29]=4)[C@@H:19]([NH:21][S:22]([CH:25]4[CH2:27][CH2:26]4)(=[O:24])=[O:23])[CH3:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:44])C=1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][C@H:18]([C:28]4[CH:29]=[CH:30][C:31]([S:34]([CH3:35])=[O:44])=[CH:32][CH:33]=4)[C@@H:19]([NH:21][S:22]([CH:25]4[CH2:26][CH2:27]4)(=[O:24])=[O:23])[CH3:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 24954947HCID 24954947, compound

Product 1

HCID 59786558HCID 59786558, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-[(1R,2S)-1-[1-(4-fluorophenyl)indazol-5-yl]oxy-1-(4-methylsulfanylphenyl)propan-2-yl]cyclopropanesulfonamide (29, 20.5 mg, 0.04 mmol) was dissolved in DCM (2 mL) and cooled in an ice bath. 3-Chloroperbenzoic acid (70-75%) (10 mg, 0.04 mmol) dissolved in DCM (0.1 mL) was added. The reaction was stirred for 30 min, quenched by addition of 10% Na2SO3 solution (0.5 mL). Purification by HPLC and freeze drying of fractions with product gave the title compound as a colourless solid. Yield 17 mg (80%).

Workup

  1. temperaturecooled in an ice bath
  2. additionwas added
  3. customquenched by addition of 10% Na2SO3 solution (0.5 mL)
  4. customPurification by HPLC
  5. customfreeze drying of fractions with product

Sources & evidence

ORD record
ord-aaa77d0843f24d029cc8a30f35e5b8e2
Source dataset
uspto-grants-2011_10
Patent number
US08030340B2

Reaction notes

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