m-Chloroperbenzoic acid → HCID 11444006, compound

HRID 2111787Notes

Reaction equation

HRID 2111787 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9]([C:11]2[CH:38]=[CH:37][C:14]3[N:15]([C:18]4[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]5[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=5)=[CH:20][CH:19]=4)[CH:16]=[N:17][C:13]=3[CH:12]=2)=[O:10])[CH:2]=1.ClC1C=C(C=CC=1)C(OO)=[O:44]>C(Cl)Cl>[O-:44][N+:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9]([C:11]2[CH:38]=[CH:37][C:14]3[N:15]([C:18]4[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]5[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:34])[F:35])=[CH:28][CH:27]=5)=[CH:20][CH:19]=4)[CH:16]=[N:17][C:13]=3[CH:12]=2)=[O:10])[CH:2]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11306914HCID 11306914, compound

Product 1

HCID 11444006HCID 11444006, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Pyridin-3-ylmethyl-1-(4-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxamide (EXAMPLE 35, 31 mg, 0.060 mmol) was dissolved in DCM (3 mL) and treated with m-chloroperoxybenzoic acid (18 mg, 0.72 mmol) and the mixture stirred at rt for 4 h. After this time the mixture was concentrated in vacuo and the crude product purified by preparative HPLC to give the title compound. 1H NMR (CD3OD, 400 MHz): δ 4.63 (s, 2H), 5.21 (s, 2H), 7.24 (d, 2H, J=9.2 Hz), 7.31 (d, 2H, J=8.4 Hz), 7.51-7.60 (m, 6H), 7.66 (d, 1H, J=8.0 Hz), 7.90 (dd, 1H, J=8.8, 1.6 Hz), 8.25 (d, 1H, J=6.0 Hz), 8.31 (s, 1H), 8.38 (s, 1H), 8.46 (s, 1H). MS (ES+); m/z 535 (100) [MH+], 536 (25) [MH+2].

Workup

  1. concentrationAfter this time the mixture was concentrated in vacuo
  2. customthe crude product purified by preparative HPLC

Sources & evidence

ORD record
ord-ae033103363142b1b9bc637973c3fa62
Source dataset
uspto-grants-2009_04
Patent number
US07521448B2

Reaction notes

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