Methanol → (S)-4-(1-Hydroxymethyl-2-phenyl-ethylamino)-3-{4-methyl-6-[4-(1-phenyl-methanoyl)-piperazin-1-yl]-1H-benzimidazol-2-yl}-1H-pyridin-2-one

HRID 1354639Notes

Reaction equation

HRID 1354639 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:11][C:12]1[CH:17]=[CH:16][NH:15][C:14](=[O:18])[C:13]=1[C:19]1[NH:23][C:22]2[CH:24]=[C:25]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[CH:26]=[C:27]([CH3:28])[C:21]=2[N:20]=1)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:35][OH:36]>C(Cl)(=O)C1C=CC=CC=1>[OH:1][CH2:2][C@@H:3]([NH:11][C:12]1[CH:17]=[CH:16][NH:15][C:14](=[O:18])[C:13]=1[C:19]1[NH:23][C:22]2[CH:24]=[C:25]([N:29]3[CH2:30][CH2:31][N:32]([C:35]([C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)=[O:36])[CH2:33][CH2:34]3)[CH:26]=[C:27]([CH3:28])[C:21]=2[N:20]=1)[CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 136191205(S)-4-(1-Hydroxymethyl-2-phenyl-ethylamino)-3-(4-methyl-6-piperazin-1-yl-1H-benzimidazol-2-yl)-1H-pyridin-2-one

Product 1

HCID 136191223(S)-4-(1-Hydroxymethyl-2-phenyl-ethylamino)-3-{4-methyl-6-[4-(1-phenyl-methanoyl)-piperazin-1-yl]-1H-benzimidazol-2-yl}-1H-pyridin-2-oneYield 33%

Reagents, catalysts & solvents 1

HCID 7412Benzoyl chlorideCatalyst

Procedure

To a solution of (S)-4-(1-hydroxymethyl-2-phenyl-ethylamino)-3-(4-methyl-6-piperazin-1-yl-1H-benzimidazol-2-yl)-1H-pyridin-2-one (30 mg, 0.063 mmol) in methanol (2 mL) was added benzoyl chloride (1 drop). The reaction mixture was stirred for 5 min. and concentrated. The residue was purified by prep. HPLC to yield the title compound (11 mg, 33%). 1H NMR (400 MHz, CD3OD) δ 7.48–7.54 (5H, m), 7.37 (1H, s), 7.13–7.26 (7H, m), 6.08 (1H, d, J=7.7 Hz), 3.79–4.02 (5H, m), 3.76 (1H, dd, J=4.7, 11.2 Hz), 3.67 (1H, dd, J 5.7, 11.2 Hz), 3.54 (4H, m), 3.03 (1H, dd, J=5.7, 13.7 Hz), 2.89 (1H, dd, J=8.0, 13.7 Hz), 2.62 (3H, s). LCMS (M+H)+ m/z 563 (t=2.19 min.).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by prep

Sources & evidence

ORD record
ord-c9b27b0f720b453ca3f980a674c20176
Source dataset
uspto-grants-2007_05
Patent number
US07223757B2

Reaction notes

Loading…