Benzoyl chloride → N-Benzoyl-2-[4-(benzyloxy)phenyl]-1-cyclohexyl-1H-benzimidazol-5-sulfonamide

HRID 392991Notes

Reaction equation

HRID 392991 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:18]3[CH:26]=[CH:27][C:28]([S:30]([NH2:33])(=[O:32])=[O:31])=[CH:29][C:17]=3[N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:34](Cl)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>>[C:34]([NH:33][S:30]([C:28]1[CH:27]=[CH:26][C:18]2[N:19]([CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)[C:15]([C:12]3[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:14][CH:13]=3)=[N:16][C:17]=2[CH:29]=1)(=[O:32])=[O:31])(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

3

Reactant 2

HCID 7412Benzoyl chlorideHCID 226608052-[4-(Benzyloxy)phenyl]-1-cyclohexyl-1H-benzimidazole-5-sulfonamide

Product 1

HCID 22660823N-Benzoyl-2-[4-(benzyloxy)phenyl]-1-cyclohexyl-1H-benzimidazol-5-sulfonamideYield 21.2%

Procedure

Intermediate 69 (0.023 g, 0.05 mmol) and benzoyl chloride (0.005 ml, 0.06 mmol) were used to prepare the titled compound (0.006 g, 18%) by the same method as in example 15. 1H NMR (CDCl3) δ 8.59 (s, 1H), 8.26 (d, 1H, J=8.8 Hz), 7.84 (m, 3H), 7.59 (d, 211, J=8.8 Hz), 7.56-7.37 (m, 8H), 7.18 (d, 2H, J=8.4 Hz), 5.17 (s, 2H), 4.42 (m, 1H), 2.33 (br m, 4H), 1.99 (br m, 2H), 1.81 (br m, 1H), 1.36 (br m, 3H); ESI-MS m/e 566.1 (M+1); HPLC purity (ELSD) 100%.

Sources & evidence

ORD record
ord-1ac4b1d33aa249109abde8e80f9e823b
Source dataset
uspto-grants-2004_10
Patent number
US06803374B2

Reaction notes

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