4-(Trifluoromethoxy)benzylamine → 3-1H-indol-4-yl-1-{[4-(trifluoromethoxy)phenyl]methyl}urea

HRID 585949

Reaction equation

HRID 585949 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=1.[N:14]([C:17]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:18]=1[CH:19]=[CH:20][NH:21]2)=[C:15]=[O:16]>>[NH:21]1[C:22]2[C:18](=[C:17]([NH:14][C:15]([NH:9][CH2:8][C:7]3[CH:10]=[CH:11][C:4]([O:3][C:2]([F:12])([F:13])[F:1])=[CH:5][CH:6]=3)=[O:16])[CH:25]=[CH:24][CH:23]=2)[CH:19]=[CH:20]1

Participants

3

Reactant 2

HCID 5718464-(Trifluoromethoxy)benzylamineHCID 220326444-isocyanato-1H-indole

Product 1

HCID 100663943-1H-indol-4-yl-1-{[4-(trifluoromethoxy)phenyl]methyl}ureaYield 65.8%

Procedure

4-(Trifluoromethoxy)benzylamine (0.21 g, 1.1 mmol) and the product of Example 80A (0.16 g, 1 mmol) were treated as described in Example 80B to provide the title compound (0.23 g). mp 177° C.; 1H NMR (300 MHz, DMSO-d6) δ 4.36 (d, 2H), 6.52 (m, 1H), 6.95 (m, 3H), 7.24 (t, 1H), 7.36 (d, 2H), 7.48 (d, 2H), 7.63 (dd, 1H), 8.32 (1H), 11.06 (s, 1H); MS (DCI+) m/z 349.9 (M+H)+; Anal. Calcd. For C17H14N3F3O2: C, 58.63, H, 4.34, N, 12.07. Found: C, 58.51, H, 3.98, N, 12.03.

Sources & evidence

ORD record
ord-744b38e6056245e7aed10aceedcfd722
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Linked notes

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