m-Chloroperbenzoic acid → HCID 68006866, compound

HRID 2402092Notes

Reaction equation

HRID 2402092 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:10]([C:35]#[N:36])=[C:11]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C:32](=[O:34])[CH3:33])[CH:26]=3)[S:12][C:13]=2[C:14]2[N:18]=[CH:17][N:16]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)[N:15]=2)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:45])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:9]2[C:10]([C:35]#[N:36])=[C:11]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C:32](=[O:34])[CH3:33])[CH:26]=3)[S:12][C:13]=2[C:14]2[N:18]=[CH:17][N:16]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)[N:15]=2)=[O:45])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68006691HCID 68006691, compound

Product 1

HCID 68006866HCID 68006866, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(4-{4-[(4-chlorophenyl)sulfanyl]-3-cyano-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-2-thienyl}pyridin-2-yl)acetamide (0.0575 g, 0.107 mmol) was dissolved in methylene chloride (5.00 mL), followed by addition of m-chloroperbenzoic acid (0.0194 g, 0.112 mmol). The reaction mixture was stirred at room temperature for 1 hr. The solution was concentrated, and purified by column chromatography. The eluent was 50-100% ethyl acetate in hexane to yield a solid product (0.0324 g, 54.7%) LCMS: (AA) ES+ 553, 555. 1H NMR (300 MHz, CDCl3) δ: 8.47 (m, 2H), 8.41 (s, 1H), 8.36 (d, 1H), 8.06 (dd, 2H), 7.46 (dd, 2H), 7.45 (d, 1H), 5.53-5.59 (dd, 1H), 4.08-4.16 (m, 1H), 3.73-3.81 (m, 1H), 2.25 (s, 3H), 2.10-2.18 (m, 1H), 2.00-2.07 (m, 2H), 1.69-1.80 (m, 3H).

Workup

  1. concentrationThe solution was concentrated
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-30b9546ce2564c7882ba82cd535a5114
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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