4-Fluorophenyl isocyanate → 6-Chloro-4-[4-(4-fluorophenylaminocarbonyl)piperazin-1-yl]quinoline

HRID 1353311Notes

Reaction equation

HRID 1353311 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.[F:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[O:27])=[CH:21][CH:20]=1.CCCCCC.CCOC(C)=O>CN(C1C=CN=CC=1)C.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[N:12]1[CH2:13][CH2:14][N:15]([C:26]([NH:25][C:22]2[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=2)=[O:27])[CH2:16][CH2:17]1

Participants

6

Reactant 3

HCID 709554-Fluorophenyl isocyanateHCID 114706516-Chloro-4-(piperazin-1-yl)quinolineHCID 21226206Ethyl acetate hexane

Product 1

HCID 211017366-Chloro-4-[4-(4-fluorophenylaminocarbonyl)piperazin-1-yl]quinoline

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

6-Chloro-4-(piperazin-1-yl)quinoline (0.25 g, 1.0 mmol), 4-fluorophenyl isocyanate (170 μL, 1.5 mmol), and DMAP (2 mg) in THF (10 mL) are reacted according to method C yielding the product as a colorless solid after column chromatography with hexane-EtOAc. 1H NMR ([D]6-DMSO), δ 3.17 (m, 4H), 3.75 (m, 4H), 7.08 (t, 2H), 7.10 (d, 1H), 7.46 (dd, 2H), 7.72 (dd, 1H), 7.98 (d, 1H), 8.01 (d, 1H), 8.68 (br. s, 1H), 8.72 (d, 1H).

Sources & evidence

ORD record
ord-02797a29beb744f98af12ba6c8cd9b69
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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