Methanol → HCID 57942467, compound

HRID 1438577Notes

Reaction equation

HRID 1438577 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:21](COC)[S:22]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[C:27]([C:32]([F:35])([F:34])[F:33])[CH:26]=2)(=[O:24])=[O:23])[C:5]([C:8]([C:10]2[C:18]3[N:17]([CH3:19])[C:16](=[O:20])[NH:15][C:14]=3[CH:13]=[CH:12][CH:11]=2)=[O:9])=[N:6][CH:7]=1.O.CO>Cl.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:21][S:22]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[C:27]([C:32]([F:35])([F:33])[F:34])[CH:26]=2)(=[O:23])=[O:24])[C:5]([C:8]([C:10]2[C:18]3[N:17]([CH3:19])[C:16](=[O:20])[NH:15][C:14]=3[CH:13]=[CH:12][CH:11]=2)=[O:9])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 962Water2×HCID 57942544HCID 57942544, compound

Product 1

HCID 57942467HCID 57942467, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of N-[5-Chloro-2-(3-methyl-2-oxo-2,3-dihydro-1H-benzoimidazole-4-carbonyl)-pyridin-3-yl]-N-methoxymethyl-4-methyl-3-trifluoromethyl-benzenesulfonamide in 4 M HCl in dioxane (2 mL) and water (1 mL) was heated at 95° C. for 7 h, then MeOH (1 mL) and water (2 mL) was added and heating was continued overnight. The resulting mixture was purified by HPLC to provide N-[5-chloro-2-(3-methyl-2-oxo-2,3-dihydro-1H-benzoimidazole-4-carbonyl)-pyridin-3-yl]-4-methyl-3-trifluoromethyl-benzenesulfonamide. 1H NMR (400 MHz, CDCl3) δ 10.94 (s, 1 H), 8.28 (d, J=2.0 Hz, 1 H), 8.21 (d, J=1.6 Hz, 1H), 8.08 (s, 1 H), 7.95 (d, J=7.6 Hz, 1 H), 7.42 (d, J=8.0 Hz, 1 H), 7.19-7.17 (m, 1 H), 7.01 (t, J=7.6 Hz, 1 H), 6.82 (d, J=7.6 Hz, 1 H), 3.10 (s, 3 H), 2.53 (s, 3H); MS m/z 524.9 (M+H)+.

Workup

  1. temperatureheating
  2. customThe resulting mixture was purified by HPLC

Sources & evidence

ORD record
ord-8cd6084b149f43ee9e53dacb321fc925
Source dataset
uspto-grants-2009_11
Patent number
US07622583B2

Reaction notes

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