2-Chloro-4-(trifluoromethyl)phenyl isocyanate → 1-(2-Chloro-4-trifluoromethyl-phenyl)-3-[3-(2-isopropyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-urea

HRID 919482Notes

Reaction equation

HRID 919482 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[CH:10]=[C:11]([NH2:17])[CH:12]=[CH:13][C:14]=2[O:15][CH3:16])=[CH:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].[Cl:18][C:19]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:20]=1[N:29]=[C:30]=[O:31]>C(Cl)Cl>[Cl:18][C:19]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:20]=1[NH:29][C:30]([NH:17][C:11]1[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:9]([C:8]2[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=[CH:6][CH:7]=2)[CH:10]=1)=[O:31]

Participants

4

Reactant 2

HCID 51025332-Chloro-4-(trifluoromethyl)phenyl isocyanateHCID 231395083-(2-isopropyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine

Product 1

HCID 117051231-(2-Chloro-4-trifluoromethyl-phenyl)-3-[3-(2-isopropyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-ureaYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2-isopropyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine (0.1 g, 0.433 mmol) in CH2Cl2, was added 2-Chloro-4-trifluoromethylphenyl isocyanate (0.106 g, 0.476 mmol) and stirred overnight. The resulting precipitate was filtered and washed with methylene chloride/hexane (1:1), and dried in vacuo to yield Compound 48 as a colorless solid (0.109 g, 56%). LCMS m/z (%)=455 M+H+ (37Cl, 35), 453 M+H+ (35Cl, 100), 1H NMR (400 MHz, acetone-d6) δ: 8.78 (bs, 1H), 8.48 (d, J=8.97 Hz, 1H), 7.99 (bs, 1H), 7.615 (s, 1H), 7.52-7.46 (m, 1H), 7.375 (d, J=1.41 Hz, 1H), 7.337 (d, J=2.64 Hz, 1H), 6.973 (d, J=8.92 Hz, 1H), 6.027 (d, J=1.63 Hz, 1H), 4.151 (m, 1H), 3.676 (s, 3H), 1.244 (d, J=6.61 Hz, 6H).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with methylene chloride/hexane (1:1)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-5c1a7a2142a741609fa7b6e28efdb8d9
Source dataset
uspto-grants-2016_03
Patent number
US09273035B2

Reaction notes

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