Phenyl isocyanate → N-[(4-{[benzyl({[3,5-bis(trifluoromethyl)benzoyl]amino}sulfonyl)amino]methyl}cyclohexyl)methyl]-N'-phenylurea

HRID 23740Notes

Reaction equation

HRID 23740 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][N:10]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[S:11]([NH:14][C:15](=[O:30])[C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=2)(=[O:13])=[O:12])[CH2:5][CH2:4]1.[C:38]1([N:44]=[C:45]=[O:46])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>ClCCl>[CH2:31]([N:10]([CH2:9][CH:6]1[CH2:5][CH2:4][CH:3]([CH2:2][NH:1][C:45]([NH:44][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:46])[CH2:8][CH2:7]1)[S:11]([NH:14][C:15](=[O:30])[C:16]1[CH:17]=[C:18]([C:26]([F:27])([F:28])[F:29])[CH:19]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:21]=1)(=[O:12])=[O:13])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 22574488N-{[4-(aminomethyl)cyclohexyl]methyl}-N-benzyl-N'-[3,5-bis(trifluoromethyl)benzoyl]sulfamide

Product 1

HCID 12997439N-[(4-{[benzyl({[3,5-bis(trifluoromethyl)benzoyl]amino}sulfonyl)amino]methyl}cyclohexyl)methyl]-N'-phenylurea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Amine (22) (25.2 mg, 46 μmole, 1.0 eq) was suspended in dichloromethane, then triethylamnine (16 μL, 114 μmole, 2.5 eq) and phenyl isocyanate (6 μL, 55 μmole, 1.2 eq) were added and the reaction stirred overnight. Silica gel chromatography provided the title compound. 1H NMR (500 MHz, DMSO-d6): δ 12.46 (s, 1H), 8.45 (s, 2H), 8.27 (s, 1H), 8.23 (s, 1H), 7.36 (d, 2H), 7.32 (d, 2H), 7.25 (t, 2H), 7.18 (m, 4H), 6.84 (t, 1H), 6.05 (t, 1H), 4.43 (s, 2H), 3.30 (water), 3.03 (s, 2H), 2.81 (t, 2H), 2.48 (DMSO), 1.60 (m, 4H), 1.30 (m, 1H), 1.21 (m, 1H), 0.64 (m, 4H).

Workup

  1. additionwere added

Sources & evidence

ORD record
ord-38234f7156f5428290c70453db61b84b
Source dataset
uspto-grants-2005_02
Patent number
US06852738B2

Reaction notes

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