2,4-Difluorophenyl isocyanate → 1-[3-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)urea

HRID 540532Notes

Reaction equation

HRID 540532 reaction equation
[Cl:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[C:8]1[CH:9]=[C:10]([NH2:16])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15].[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[N:25]=[C:26]=[O:27]>>[Cl:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[C:8]1[CH:9]=[C:10]([NH:16][C:26]([NH:25][C:19]2[CH:20]=[CH:21][C:22]([F:24])=[CH:23][C:18]=2[F:17])=[O:27])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15]

Participants

3

Reactant 2

HCID 5932582,4-Difluorophenyl isocyanateHCID 231395183-(4-Chloro-2-methyl-2H-pyrazol-3-yl)4-methoxy-phenylamine

Product 1

HCID 116755501-[3-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)ureaYield 36%

Procedure

3-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine was treated with 2,4-difluorophenyl isocyanate in a similar manner as described in Example 1.53, providing 26.7 mg (36%) of Compound 29: LCMS m/z (%)=395 (M+H37Cl, 35), 393 (M+H35Cl, 100). 1H NMR (400 MHz, DMSO-d6) δ: 9.00 (s, 1H), 8.43 (s, 1H), 8.03 (m, J1=12 Hz, J2=4 Hz, 1H), 7.56 (s, 1H), 7.50 (dd, J1=8 Hz, J2=4 Hz, 1H), 7.34 (d, J=4 Hz, 1H), 7.28 (m, J1=12 Hz, J2=4 Hz, 1H), 7.12 (d, J=8 Hz, 1H), 7.01 (m, J1=8 Hz, J2=2 Hz, 1H), 3.72 (s, 3H), 3.56 (s, 3H).

Sources & evidence

ORD record
ord-56d1422fd40c42c2aa69c8741024ee75
Source dataset
uspto-grants-2014_10
Patent number
US08871797B2

Reaction notes

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