4-Fluoro-3-(trifluoromethyl)phenyl isocyanate → 3-(4-Fluoro-3-trifluoromethyl-Phenyl)-1-methyl-1-{4-[4-(4-ethyl-piperazin-1-yl)-phenylamino]-[1,3,5]triazin-2-yl}-urea

HRID 1038745Notes

Reaction equation

HRID 1038745 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH3:23])[CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[N:6]=[CH:5][N:4]=1.[F:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]=[C:32]=[O:33])=[CH:27][C:26]=1[C:34]([F:37])([F:36])[F:35]>C1COCC1.C1(C)C=CC=CC=1>[F:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:33])[N:2]([CH3:1])[C:3]2[N:8]=[C:7]([NH:9][C:10]3[CH:11]=[CH:12][C:13]([N:16]4[CH2:17][CH2:18][N:19]([CH2:22][CH3:23])[CH2:20][CH2:21]4)=[CH:14][CH:15]=3)[N:6]=[CH:5][N:4]=2)=[CH:27][C:26]=1[C:34]([F:35])([F:36])[F:37]

Participants

5

Reactant 2

HCID 27333834-Fluoro-3-(trifluoromethyl)phenyl isocyanateHCID 66669998N-Methyl-N'-[4-(4-ethyl-piperazin-1-yl)-phenyl]-[1,3,5]triazine-2,4-diamine

Product 1

HCID 577102343-(4-Fluoro-3-trifluoromethyl-Phenyl)-1-methyl-1-{4-[4-(4-ethyl-piperazin-1-yl)-phenylamino]-[1,3,5]triazin-2-yl}-urea

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-methyl-N′-[4-(4-ethyl-piperazin-1-yl)-phenyl]-[1,3,5]triazine-2,4-diamine (24 mg, 0.077 mmol) in 1.5 ml THF and 2.5 ml toluene, 4-fluoro-3-trifluoromethyl-phenyl-isocyanate (25 μl, 0.17 mmol) is added and the mixture is stirred for 5 h at 100° C. Workup analogously as described in Example 171 gives the title compound: ESI-MS: 519 [MH]+; tR=4.3 min (purity: 100%, gradient J); TLC: Rf=0.43 (DCM/MeOH 9).

Sources & evidence

ORD record
ord-0563d810177a407a9a0c7fe5a9ea128b
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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