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

HRID 407448Notes

Reaction equation

HRID 407448 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].[F:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[O:27])=[CH:21][CH:20]=1>C(Cl)Cl>[F:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:17][C:11]2[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:9]([C:8]3[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=[CH:6][CH:7]=3)[CH:10]=2)=[O:27])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 231395083-(2-isopropyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine

Product 1

HCID 117104061-(4-Fluoro-phenyl)-3-[3-(2-isopropyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-ureaYield 31.3%

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 4-fluoro phenyl isocyanate (0.0652 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 44 as a colorless solid (0.050 g, 30%). LCMS m/z (%)=369 M+H+, (100), 1H NMR (400 MHz, DMSO-d6) δ: 8.59 (bs, 1H), 8.52 (bs, 1H), 7.42-7.35 (m, 4H), 7.28-7.27 (d, J=2.7 Hz, 1H), 7.057 (m, 3H), 6.07 (d, J=1.76 Hz, 1H), 4.10 (m, 1H), 3.66 (s, 3H), 1.24 (d, J=6.56 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-93b693f5720e47029aa3c91cf8fabb0e
Source dataset
uspto-grants-2014_06
Patent number
US08754238B2

Reaction notes

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