Trifluoroacetic acid → 7-Chloro-4-[4-(4-fluorophenylaminocarbonyl)-2-methylpiperazin-1-yl]quinoline

HRID 1353354Notes

Reaction equation

HRID 1353354 reaction equation
C([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]3[C:18](=[CH:19][C:20]([Cl:24])=[CH:21][CH:22]=3)[N:17]=[CH:16][CH:15]=2)[CH:10]([CH3:25])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.[F:33][C:34]1[CH:39]=[CH:38][C:37]([N:40]=C=O)=[CH:36][CH:35]=1>C(Cl)Cl>[Cl:24][C:20]1[CH:19]=[C:18]2[C:23]([C:14]([N:11]3[CH2:12][CH2:13][N:8]([C:6]([NH:40][C:37]4[CH:38]=[CH:39][C:34]([F:33])=[CH:35][CH:36]=4)=[O:5])[CH2:9][CH:10]3[CH3:25])=[CH:15][CH:16]=[N:17]2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 709554-Fluorophenyl isocyanateHCID 211017004-[4-(tert-Butoxycarbonyl)-2-methylpiperazin-1-yl]-7-chloroquinoline

Product 1

HCID 211017717-Chloro-4-[4-(4-fluorophenylaminocarbonyl)-2-methylpiperazin-1-yl]quinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[4-(tert-butoxycarbonyl)-2-methylpiperazin-1-yl]-7-chloroquinoline (0.30 g, 0.8 mmol) is deprotected with TFA in CH2Cl2 and transformed after being washed with base into the product according to method C using 4-fluorophenyl isocyanate (61 μL, 0.54 mmol) to give the title product a colorless solid.

Workup

  1. washafter being washed with base into the product

Sources & evidence

ORD record
ord-fe80b26363ca4a799245101af8c52490
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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