Methanol → HCID 10099592, compound

HRID 1767023Notes

Reaction equation

HRID 1767023 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([OH:38])[CH2:9][NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13](=[O:21])[C:12]=2[C:22]2[NH:26][C:25]3[CH:27]=[C:28]([N:32]4[CH2:37][CH2:36]N[CH2:34][CH2:33]4)[CH:29]=[C:30]([CH3:31])[C:24]=3[N:23]=2)[CH:5]=[CH:6][CH:7]=1.[C:39]([BH3-])#[N:40].[Na+].[CH3:43][OH:44]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([OH:38])[CH2:9][NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13](=[O:21])[C:12]=2[C:22]2[NH:26][C:25]3[CH:27]=[C:28]([N:32]4[CH2:37][CH2:36][N:40]([CH2:39][CH2:43][OH:44])[CH2:34][CH2:33]4)[CH:29]=[C:30]([CH3:31])[C:24]=3[N:23]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 10459605HCID 10459605, compound

Product 1

HCID 10099592HCID 10099592, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solutionof 12 mg (0.023 mmol) of the 4-[(S)-2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-3-(4-methyl-6-piperazin-1-yl-1H-benzimidazole-2-yl)-1H-quinoline-2-one in 0.5 mL of methanol was added ˜5 mg of glycaldehyde to which was added 0.3 mL of 1 N solution of sodiumcyanoborohydride in tetrahydrofuran, and the mixture was stirred for 30 minutes, and then it was subjected to preparative HPLC to afford the product. LRMS [M+H]+573; 1H NMR (400 MHz, CDCl3) δ 8.06 (d, 1H, J=7.96 Hz), 7.97 (s, 1H), 7.64 (dd, 1H, J=7.97, 8.4 Hz), 7.03-7.36 (m, 7H), 4.77 (m, 1H), 3.94 (t, 1H, J=5.1 Hz), 3.42-3.52(m, 8H), 3.36 (t, 1H, J=5.1 Hz), 3.31-3.47 (m, 4H), 2.63 (s, 3H).

Workup

  1. customto afford the product

Sources & evidence

ORD record
ord-7e589278aafe43969c7ecfb5c745312d
Source dataset
uspto-grants-2007_06
Patent number
US07232826B2

Reaction notes

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