4-Fluorophenyl isocyanate → HCID 21101782, compound

HRID 1353313Notes

Reaction equation

HRID 1353313 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[CH:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]=[C:27]=[O:28])=[CH:22][CH:21]=1.CCCCCC.CCOC(C)=O>CN(C1C=CN=CC=1)C.C1COCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:13]3[CH2:18][CH2:17][N:16]([C:27]([NH:26][C:23]4[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=4)=[O:28])[CH2:15][CH2:14]3)=[CH:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 709554-Fluorophenyl isocyanateHCID 21101958HCID 21101958, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 21101782HCID 21101782, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

7-Chloro-2-methyl-4-(piperazin-1-yl)quinoline (0.26 g), 4-fluorophenyl isocyanate (114 μL, 1.0 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 2.58 (s, 3H), 3.17 (m, 4H), 3.71 (m, 4H), 6.94 (s, 1H), 7.06 (t, 2H), 7.46 (m, 3H), 7.87 (d, 1H), 8.01 (d, 1H), 8.68 (br. s, 1H).

Sources & evidence

ORD record
ord-b5ee7adfab964c6882121ca85c46ad67
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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