Diisopropylethylamine → 4-(7-Chloro-4-quinolinyl)-N-[4-(trifluoromethyl)cyclohexyl]-1-piperazinecarboxamide

HRID 1353413Notes

Reaction equation

HRID 1353413 reaction equation
[F:1][C:2]([F:11])([F:10])[CH:3]1[CH2:8][CH2:7][CH:6]([NH2:9])[CH2:5][CH2:4]1.Cl[C:13](OC1C=CC([N+]([O-])=O)=CC=1)=[O:14].C(N(C(C)C)CC)(C)C.[Cl:34][C:35]1[CH:44]=[C:43]2[C:38]([C:39]([N:45]3[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]3)=[CH:40][CH:41]=[N:42]2)=[CH:37][CH:36]=1>C(Cl)Cl.CO>[Cl:34][C:35]1[CH:44]=[C:43]2[C:38]([C:39]([N:45]3[CH2:50][CH2:49][N:48]([C:13]([NH:9][CH:6]4[CH2:5][CH2:4][CH:3]([C:2]([F:10])([F:11])[F:1])[CH2:8][CH2:7]4)=[O:14])[CH2:47][CH2:46]3)=[CH:40][CH:41]=[N:42]2)=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 7383897-Chloro-4-(piperazin-1-yl)quinolineHCID 13714353cis-4-(Trifluoromethyl)cyclohexylamine

Product 1

HCID 211017294-(7-Chloro-4-quinolinyl)-N-[4-(trifluoromethyl)cyclohexyl]-1-piperazinecarboxamide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

As described for example 78, 4-trifluoromethyl cyclohexyl amine, 4-nitrophenyl chloroformate, diisopropyl(ethyl)amine, and 7-chloro-4-(piperazin-1-yl)quinoline are reacted to afford the product after flash chromatography with CH2Cl2-MeOH. LC-MS: 441 (M++1). 1H NMR (CDCl3) δ 8.78 (d, 1H), 8.05 (s, 1H), 7.95 (d, 1H), 7.46 (d, 1H), 6.85 (d, 1H), 4.60 (d, 1H), 4.03 (m, 1H), 3.65 (m, 4H), 3.20 (m, 4H), 2.10 (m, 1H), 1.85 (m, 4H), 1.50–1.70 (m, 4H).

Workup

  1. customare reacted

Sources & evidence

ORD record
ord-3bf660344e534bd49abbe9af16720a11
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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