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

HRID 919487Notes

Reaction equation

HRID 919487 reaction equation
[Br:1][C:2]1[CH:6]=[N:5][N:4]([CH:7]([CH3:9])[CH3:8])[C:3]=1[C:10]1[CH:11]=[C:12]([NH2:18])[CH:13]=[CH:14][C:15]=1[O:16][CH3:17].Cl[C:20]1[CH:21]=[C:22]([N:30]=[C:31]=[O:32])[CH:23]=[CH:24][C:25]=1[C:26]([F:29])([F:28])[F:27].C(Cl)[Cl:34]>>[Br:1][C:2]1[CH:6]=[N:5][N:4]([CH:7]([CH3:9])[CH3:8])[C:3]=1[C:10]1[CH:11]=[C:12]([NH:18][C:31]([NH:30][C:22]2[CH:23]=[CH:24][C:25]([C:26]([F:29])([F:28])[F:27])=[CH:20][C:21]=2[Cl:34])=[O:32])[CH:13]=[CH:14][C:15]=1[O:16][CH3:17]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 143684972-Chloro-4-isocyanato-1-(trifluoromethyl)benzeneHCID 231394423-(4-bromo-2-isopropyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine

Product 1

HCID 115773681-[3-(4-Bromo-2-isopropyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2Chloro-4-trifluoromethyl-phenyl)-ureaYield 73%

Procedure

To a solution of 3-(4-bromo-2-isopropyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine (0.08 g, 0.258 mmol) in CH2Cl2, was added 3-chloro-4-trifluoromethyl-phenyl isocyanate (0.059 g, 0.263 mmol) and stirred overnight at ambient temperature. The resulting precipitate was filtered and washed with methylene chloride/hexane (1:1), and dried in vacuo to yield Compound 53 as a colorless solid (0.1 g, 73%). LCMS m/z (%)=535 M+H+ (81Br 37 Cl, 39), 533 M+H+ (81Br 35Cl, 100), 531 M+H+ (79Br 35Cl, 63), 1H NMR (400 MHz, DMSO-d6) δ: 8.582 (bs, 1H), 8.456 (bs, 1H), 7.864 (s, 1H), 7.654 (d, J=8.28 Hz, 1H), 7.557 (d, J=2.76 Hz, 1H), 7.536 (d, J=2.76 Hz, 1H), 7.369 (d, J=9.13 Hz, 1H), 4.133 (m, 1H), 3.752 (s, 3H), 1.375 (d, J=6.61 Hz, 3H), 1.217 (d, J=6.61 Hz, 3H).

Workup

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

Sources & evidence

ORD record
ord-8554f21c596045a9bd2a1d8eed5e9b68
Source dataset
uspto-grants-2016_03
Patent number
US09273035B2

Reaction notes

Loading…