3,5-Bis(trifluoromethyl)phenyl isocyanate → HCID 11363880, compound

HRID 407427Notes

Reaction equation

HRID 407427 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]([F:33])([F:32])[C:19]1[CH:20]=[C:21]([N:29]=[C:30]=[O:31])[CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1>>[F:17][C:18]([F:32])([F:33])[C:19]1[CH:20]=[C:21]([NH:29][C:30]([NH:16][C:10]2[CH:11]=[CH:12][C:13]([O:14][CH3:15])=[C:8]([C:3]3[N:4]([CH3:7])[N:5]=[CH:6][C:2]=3[Cl:1])[CH:9]=2)=[O:31])[CH:22]=[C:23]([C:25]([F:28])([F:26])[F:27])[CH:24]=1

Participants

3

Reactant 2

HCID 27333143,5-Bis(trifluoromethyl)phenyl isocyanateHCID 231395183-(4-Chloro-2-methyl-2H-pyrazol-3-yl)4-methoxy-phenylamine

Product 1

HCID 11363880HCID 11363880, compoundYield 32%

Procedure

3-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine was treated with 3,5-Bis(trifluoromethyl)phenyl isocyanate in a similar manner as described in Example 1.53, providing 21.5 mg (32%) of Compound 82: LCMS m/z (%)=495 (M+H37Cl, 41), 493 (M+H35Cl, 100). 1H NMR (400 MHz, DMSO-d6) δ: 9.58 (s, 1H), 9.18 (s, 1H), 8.31 (s, 2H), 7.80 (s, 1H), 7.79 (s, 1H), 7.79 (dd, J1=8 Hz, J2=4 Hz, 1H), 7.59 (d, J=2 Hz, 1H), 7.36 (d=8 Hz, 1H), 3.96 (s, 3H), 3.80 (s, 3H).

Sources & evidence

ORD record
ord-db1ad1f55c944ea69c8f98d318b75689
Source dataset
uspto-grants-2014_06
Patent number
US08754238B2

Reaction notes

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