Diisopropylcarbodiimide → 4-Chloro-5-[5-chloro-1-methyl-6-(4-(trifluoromethyl)piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino]-2-fluorobenzonitrile

HRID 1258737Notes

Reaction equation

HRID 1258737 reaction equation
[Cl:1][C:2]1[C:9]([N:10]=[C:11]=S)=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:13])[CH:3]=1.[Cl:14][C:15]1[C:16]([N:24]2[CH2:29][CH2:28][CH:27]([C:30]([F:33])([F:32])[F:31])[CH2:26][CH2:25]2)=[CH:17][C:18]([NH:22][CH3:23])=[C:19]([CH:21]=1)[NH2:20].CC(C)N=C=NC(C)C>CN(C=O)C>[Cl:1][C:2]1[C:9]([NH:10][C:11]2[N:22]([CH3:23])[C:18]3[CH:17]=[C:16]([N:24]4[CH2:29][CH2:28][CH:27]([C:30]([F:32])([F:33])[F:31])[CH2:26][CH2:25]4)[C:15]([Cl:14])=[CH:21][C:19]=3[N:20]=2)=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:13])[CH:3]=1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 679581715-Chloro-2-methylamino-4-(4-trifluoromethyl-piperidin-1-yl)anilineHCID 866463424-Chloro-2-fluoro-5-isothiocyanatobenzonitrile

Product 1

HCID 866743494-Chloro-5-[5-chloro-1-methyl-6-(4-(trifluoromethyl)piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino]-2-fluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The sub-title compound was prepared in analogy to the procedure in Example 76 using 4-chloro-2-fluoro-5-isothiocyanatobenzonitrile (300 mg; 1.41 mmol), 5-chloro-2-methylamino-4-(4-trifluoromethyl-piperidin-1-yl)aniline (434 mg; 1.41 mmol), DIC (178 mg; 1.41 mmol) and DMF (12 mL).

Sources & evidence

ORD record
ord-573513786ea2433cb53379cbf5cb6fad
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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