4-Chlorophenyl Isocyanate → 1-(4-Chloro-phenyl)3-[4-methoxy-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-urea

HRID 540528Notes

Reaction equation

HRID 540528 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[C:10]1[N:11]([CH3:15])[N:12]=[CH:13][CH:14]=1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[O:25])=[CH:19][CH:18]=1>C(Cl)Cl>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([C:10]3[N:11]([CH3:15])[N:12]=[CH:13][CH:14]=3)[CH:5]=2)=[O:25])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 231394504-methoxy-3-(2-methyl-2H-pyrazol-3-yl)phenylamine

Product 1

HCID 117101541-(4-Chloro-phenyl)3-[4-methoxy-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-ureaYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methoxy-3-(2-methyl-2H-pyrazol-3-yl)-phenylamine (0.291 g, 1.43 mmol) was treated with 4-chlorophenyl isocyanate (0.247 g, 1.57 mmol, 1.1 equiv.) in CH2Cl2 (5 mL), in a similar manner as described in Example 1.2 to afford Compound 75 (0.415 g, 1.16 mmol, 81%) as a white solid. LCMS m/z (%)=357 (M+H). 1H NMR (400 MHz, acetone-d6) δ: 8.21 (s, 1H), 8.07 (s, 1H), 7.58 (dd, J=2.8, 8.9 Hz, 1H), 7.56 (d, J=8.8 Hz, 2H), 7.44 (d, J=2.7 Hz, 1H), 7.39 (d, J=1.8 Hz, 1H), 7.28 (d, J=8.8 Hz, 2H), 7.08 (d, J=8.9 Hz, 1H), 6.20 (d, J=1.8 Hz, 1H), 3.81 (s, 3H), 3.68 (s, 3H).

Sources & evidence

ORD record
ord-3c16b429b0694ae4a73218ec3dca6560
Source dataset
uspto-grants-2014_10
Patent number
US08871797B2

Reaction notes

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