HCID 21875921, compound → HCID 22291355, compound

HRID 967850Notes

Reaction equation

HRID 967850 reaction equation
[CH2:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][NH:16][C:17]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])=[O:18])=[CH:10][CH:9]=2)[C:6]2[CH:30]=[CH:31][CH:32]=[CH:33][C:5]=2[N:4]=1)[CH3:2]>Cl.CO.[Pt](=O)=O>[CH2:1]([C:3]1[N:7]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][NH:16][C:17]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])=[O:18])=[CH:12][CH:13]=2)[C:6]2[CH2:30][CH2:31][CH2:32][CH2:33][C:5]=2[N:4]=1)[CH3:2]

Participants

5

Reactant 1

HCID 21875921HCID 21875921, compound

Product 1

HCID 22291355HCID 22291355, compoundYield 19.3%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of 2-Ethyl-1-(4-{2-[({[(4-methylphenyl)sulfonyl]amino}carbonyl) amino]ethyl}phenyl)-1H-benzimidazole (100 mg, 0.20 mmol) and platinum (IV) oxide (22 mg, 0.096 mmol) in 2 M HCl (10 mL) and CH3OH (2 mL) was stirred for 8 h under hydrogen atmosphere (3 kgf/cm2). The mixture was filtered through a pad of Celite and the filtrate was concentrated. The crude product was purified by TLC with ethyl acetate/ethanol (10:1) to afford 18 mg (14%) of the title compound as colorless solid: MS (ESI) m/z 467 [M+H]+, 465 [M−H]−, 1H-NMR (CDCl3)δ1.15 (3H, t, J=7.6 Hz), 1.78 (2H, br), 2.26 (2H, br), 2.41 (3H, s), 2.55 (2H, q, J=7.6 Hz), 2.65 (2H, br), 2.83 (2H, br), 2.86 (2H, m), 3.49 (2H, m), 6.71 (1H, br), 7.10 (2H, d, J=8.4 Hz), 7.28 (4H, m), 7.79 (2H, d, J=8.2 Hz).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated
  3. customThe crude product was purified by TLC with ethyl acetate/ethanol (10:1)

Sources & evidence

ORD record
ord-a1ecf12ed3b0444395b4c928e9a57035
Source dataset
uspto-grants-2005_10
Patent number
US06956050B2

Reaction notes

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