3-Fluorophenyl isocyanate → 1-[3-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(3-fluoro-phenyl)-urea

HRID 407416Notes

Reaction equation

HRID 407416 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:19]=[C:20]([N:24]=[C:25]=[O:26])[CH:21]=[CH:22][CH:23]=1>>[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:25]([NH:24][C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([F:17])[CH:19]=2)=[O:26])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15]

Participants

3

Reactant 2

HCID 1230643-Fluorophenyl isocyanateHCID 231395183-(4-Chloro-2-methyl-2H-pyrazol-3-yl)4-methoxy-phenylamine

Product 1

HCID 116536771-[3-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(3-fluoro-phenyl)-ureaYield 1%

Procedure

3-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine was treated with 3-Fluorophenyl isocyanate in a similar manner to as described in Example 1.53, providing 0.5 mg (1%) of Compound 36: LCMS m/z (%)=377 (M+H37Cl, 40), 375 (M+H35Cl, 100). 1H NMR (400 MHz, acetone-d6) δ: 8.23 (s, 1H), 7.45 (dt, J1=12, J2=4, J3=2 Hz, 1H), 7.37 (s, 1H), 7.32 (s, 1H), 7.17 (d, J=24 Hz, 1H), 7.15 (dd, J1=8 Hz, J2=2 Hz, 1H), 7.03 (dd, J1=8 Hz, J2=4 Hz, 1H), 6.77 (d, J=2 Hz, 1H), 6.63 (td, J1=8 Hz, J2=4 Hz, 1H), 3.68 (s, 3H), 3.52 (s, 3H).

Sources & evidence

ORD record
ord-067c1d98659d4d90b6d8a112f9de194b
Source dataset
uspto-grants-2014_06
Patent number
US08754238B2

Reaction notes

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