Benzoyl chloride → (4-{[Benzyl({[3,5-bis(trifluoromethyl)benzoyl]amino}sulfonyl)amino]methyl}cyclohexyl)methyl benzylcarbamate

HRID 23732

Reaction equation

HRID 23732 reaction equation
[C:1]([O:9][CH2:10][CH:11]1[CH2:16][CH2:15][CH:14]([CH2:17][N:18]([CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[S:19]([NH:22][C:23](=[O:38])[C:24]2[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=2)(=[O:21])=[O:20])[CH2:13][CH2:12]1)(=[O:8])C1C=CC=CC=1.[CH2:46]([N:53]=C=O)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.C(Cl)(=O)C1C=CC=CC=1>>[CH2:46]([NH:53][C:1](=[O:8])[O:9][CH2:10][CH:11]1[CH2:12][CH2:13][CH:14]([CH2:17][N:18]([CH2:39][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[S:19]([NH:22][C:23](=[O:38])[C:24]2[CH:25]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:27]=[C:28]([C:30]([F:32])([F:31])[F:33])[CH:29]=2)(=[O:21])=[O:20])[CH2:15][CH2:16]1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

4

Reactant 3

HCID 7412Benzoyl chlorideHCID 76639Benzyl isocyanateHCID 22574465(4-{[Benzyl({[3,5-bis(trifluoromethyl)benzoyl]amino}sulfonyl)amino]methyl}cyclohexyl)methyl benzoate

Product 1

HCID 22574464(4-{[Benzyl({[3,5-bis(trifluoromethyl)benzoyl]amino}sulfonyl)amino]methyl}cyclohexyl)methyl benzylcarbamate

Procedure

Following procedure to make (5), benzyl isocyanate was substituted for benzoyl chloride to give the title compound after purification. 1H NMR: (500 MHz, DMSO-d6): δ 12.43 (s, 1H), 8.45 (s, 2H), 8.31 (s, 1H), 7.58 (t, 1H), 7.35 (d, 2H), 7.27 (t, 4H), 7.19 (t, 3H), 4.48 (s, 2H), 4.13 (d, 2H), 3.68 (d, 2H), 3.30 (water), 3.12 (d, 2H), 2.48 (DMSO), 1.62 (m, 4H), 1.45 (m, 1H), 1.37 (m, 1H), 0.63 (m, 4H).

Sources & evidence

ORD record
ord-9f207e1cca4349f093b5bf94c755006e
Source dataset
uspto-grants-2005_02
Patent number
US06852738B2

Linked notes

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