Sodium Hydroxide → HCID 178484897, compound

HRID 1354644Notes

Reaction equation

HRID 1354644 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([O:34]C)[CH2:11][NH:12][C:13]2[CH:18]=[CH:17][NH:16][C:15](=[O:19])[C:14]=2[C:20]2[NH:21][C:22]3[CH:28]=[C:27]([C:29]([NH:31][CH3:32])=[NH:30])[CH:26]=[C:25]([CH3:33])[C:23]=3[N:24]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([OH:34])[CH2:11][NH:12][C:13]2[CH:18]=[CH:17][NH:16][C:15](=[O:19])[C:14]=2[C:20]2[NH:21][C:22]3[CH:28]=[C:27]([C:29]([NH:31][CH3:32])=[NH:30])[CH:26]=[C:25]([CH3:33])[C:23]=3[N:24]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178484898HCID 178484898, compound

Product 1

HCID 178484897HCID 178484897, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-{4-[2-(3-chloro-4-methoxy-phenyl)-2-methoxy-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-7,N-dimethyl-3H-benzimidazole-5-carboxamidine (40 mg, 0.08 mmol) in methanol (5 mL) was added 2 N NaOH (0.5 mL) and the reaction mixture was stirred at room temperature for 14 h. After concentration in vacuo, the residue was purified by prep. HPLC to yield the title compound (7.2 mg, 19%) as oil. 1H NMR (300 MHz, CD3OD) δ 7.78 (1H, narrow d, J=1.6 Hz), 7.52 (1H, narrow d, J=2.1 Hz), 7.30–7.36 (3H, m), 6.99 (1H, d, J=8.5 Hz), 6.27 (1H, d, J=7.6 Hz), 4.94 (1H, t, J=5.9 Hz), 3.82 (3H, s), 3.68–3.72 (2H, m), 3.13 (3H, s), 2.63 (3H, s). LCMS (M+H)+ m/z 481 (t=1.44 min.).

Workup

  1. concentrationAfter concentration in vacuo
  2. customthe residue was purified by prep

Sources & evidence

ORD record
ord-a7e622ebeced48aba5e5835e11b63ea1
Source dataset
uspto-grants-2007_05
Patent number
US07223757B2

Reaction notes

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