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

HRID 1793714Notes

Reaction equation

C([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:11]=[C:12]([CH3:37])[C:13]3[N:17]=[C:16]([C:18]4[C:19](=[O:35])[NH:20][CH:21]=[CH:22][C:23]=4[NH:24][C@H:25]([CH2:33][OH:34])[CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[NH:15][C:14]=3[CH:36]=2)[CH2:6][CH2:5]1)(=O)C.O>Cl.O1CCOCC1>[OH:34][CH2:33][C@@H:25]([NH:24][C:23]1[CH:22]=[CH:21][NH:20][C:19](=[O:35])[C:18]=1[C:16]1[NH:15][C:14]2[CH:36]=[C:10]([N:7]3[CH2:6][CH2:5][NH:4][CH2:9][CH2:8]3)[CH:11]=[C:12]([CH3:37])[C:13]=2[N:17]=1)[CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (S)-3-[6-(4-acetyl-piperazin-1-yl)-4-methyl-1H-benzimidazol-2-yl]-4-(1-hydroxymethyl-2-phenyl-ethylamino)-1H-pyridin-2-one (900 mg, 18 mmol) in 4 M HCl in dioxane (10 mL) was added water (1 mL). The reaction mixture was heated to 80° C. for 14 h and cooled to room temperature. Concentration with high vacuum gave the title compound (0.83 g, 100%) which was used for the next step without purification. LCMS (M+H)+ m/z 459 (t=1.13 min.).

Workup

temperaturecooled to room temperature
concentrationConcentration with high vacuum

Sources & evidence

ORD record: ord-e2f19c51f51d48769083a354c2fbc81b
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07081454B2

Reaction notes

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