Sodium Acetate → 1-[(4-Fluoro-2-isopropyl-phenyl)carbamothioyl]-3-[3-[3-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]propyl]urea

HRID 924239Notes

Reaction equation

HRID 924239 reaction equation
[F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:16]=[C:17]([CH2:21][CH2:22][CH2:23][NH2:24])[CH:18]=[CH:19][CH:20]=3)=[N:11]2)=[CH:6][CH:5]=1.[F:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35]([NH2:37])=[S:36])=[C:30]([CH:38]([CH3:40])[CH3:39])[CH:29]=1.[C:41]([O-])(=[O:43])C.[Na+]>>[F:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35]([NH:37][C:41]([NH:24][CH2:23][CH2:22][CH2:21][C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([C:12]3[N:13]=[CH:14][N:10]([C:7]4[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:25])[F:26])=[CH:9][CH:8]=4)[N:11]=3)[CH:16]=2)=[O:43])=[S:36])=[C:30]([CH:38]([CH3:40])[CH3:39])[CH:29]=1

Participants

4

Reactant 3

HCID 517045Sodium AcetateHCID 893732451-(4-Fluoro-2-isopropylphenyl)thioureaHCID 904043433-(3-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-1-amine

Product 1

HCID 904046731-[(4-Fluoro-2-isopropyl-phenyl)carbamothioyl]-3-[3-[3-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]propyl]urea

Procedure

The title compound was prepared as described in Example 63 using 3-(3-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-1-amine (CA18) and 1-(4-fluoro-2-isopropylphenyl)thiourea. Sodium acetate was used in place of sodium bicarbonate. The title compound was isolated as a white solid (0.140 g, 41%): 1H NMR (400 MHz, DMSO-d6) δ 11.85 (s, 1H), 10.11 (s, 1H), 9.41 (s, 1H), 8.13-8.04 (m, 2H), 8.02-7.92 (m, 2H), 7.61 (dq, J=7.8, 1.0 Hz, 2H), 7.46 (t, J=7.6 Hz, 1H), 7.43-7.31 (m, 2H), 7.15 (dd, J=10.4, 3.0 Hz, 1H), 7.10 (t, J=5.6 Hz, 1H), 7.03 (td, J=8.5, 3.0 Hz, 1H), 3.26-3.10 (m, 2H), 2.97 (pd, J=6.9, 1.6 Hz, 1H), 2.73 (dd, J=8.5, 6.7 Hz, 2H), 1.90-1.76 (m, 2H), 1.15 (d, J=6.8 Hz, 6H); 19F NMR (376 MHz, DMSO-d6) δ −56.97, −114.41; ESIMS m/z 601 ([M+H]+), 599 ([M−H]−).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-11959e4aac2f4a60921f8eabbc43ef52
Source dataset
uspto-grants-2016_03
Patent number
US09278964B2

Reaction notes

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