Acetone → (S)-4-(1-Hydroxymethyl-2-phenyl-ethylamino)-3-[6-(4-isopropyl-piperazin-1-yl)-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one

HRID 1354640Notes

Reaction equation

HRID 1354640 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][C:36]([CH3:38])=O.C1COCC1.[BH3-]C#N.[Na+]>CO>[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]([CH:36]([CH3:38])[CH3:35])[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

6

Reactant 4

HCID 180AcetoneHCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 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 136191258(S)-4-(1-Hydroxymethyl-2-phenyl-ethylamino)-3-[6-(4-isopropyl-piperazin-1-yl)-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-oneYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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 (25 mg, 0.054 mmol) in methanol (0.5 mL) was added acetone (0.25 mL) and 1 M THF solution of NaCNBH3 (0.2 mL). The reaction mixture was stirred at room temperature for 1 h and concentrated in vacuo. The residue was purified by prep. HPLC to yield the title compound (12 mg, 44%). 1H NMR (400 MHz, CD3OD) δ7.10–7.24 (6H, m), 7.08 (1H, s), 7.06 (1H, s), 6.06 (1H, d, J=7.9 Hz), 3.58–4.01 (10H, m), 3.34 (1H, m), 3.14 (1H, m), 2.98 (1H, dd, J=5.9, 13.7 Hz), 2.83 (1H, dd, J=7.9, 13.7 Hz), 2.60 (3H, s), 1.44 (6H, d, J=6.7 Hz). LCMS (M+H)+ m/z 501 (t=1.80 min.).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by prep

Sources & evidence

ORD record
ord-0155dbd4aecd4c4983c320db7121c56f
Source dataset
uspto-grants-2007_05
Patent number
US07223757B2

Reaction notes

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