Dimethylformamide → N-[4-(6-cyano-7-oxiranylmethoxyquinolin-4-yloxy)-2-fluorophenyl]-N'-(4-fluorophenyl)urea

HRID 387948Notes

Reaction equation

HRID 387948 reaction equation
CN(C)C=O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]=[C:14]=[O:15])=[CH:9][CH:8]=1.[NH2:16][C:17]1[CH:40]=[CH:39][C:20]([O:21][C:22]2[C:31]3[C:26](=[CH:27][C:28]([O:34][CH2:35][CH:36]4[CH2:38][O:37]4)=[C:29]([C:32]#[N:33])[CH:30]=3)[N:25]=[CH:24][CH:23]=2)=[CH:19][C:18]=1[F:41]>O>[C:32]([C:29]1[CH:30]=[C:31]2[C:26](=[CH:27][C:28]=1[O:34][CH2:35][CH:36]1[CH2:38][O:37]1)[N:25]=[CH:24][CH:23]=[C:22]2[O:21][C:20]1[CH:39]=[CH:40][C:17]([NH:16][C:14]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([F:6])=[CH:8][CH:9]=2)=[O:15])=[C:18]([F:41])[CH:19]=1)#[N:33]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 709554-Fluorophenyl isocyanateHCID 229362494-(4-Amino-3-fluorophenoxy)-7-oxiranylmethoxyquinoline-6-carbonitrile

Product 1

HCID 22936552N-[4-(6-cyano-7-oxiranylmethoxyquinolin-4-yloxy)-2-fluorophenyl]-N'-(4-fluorophenyl)urea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After adding dimethylformamide (2 ml) and 4-fluorophenyl isocyanate (0.15 ml) to 4-(4-amino-3-fluorophenoxy)-7-oxiranylmethoxy-quinoline-6-carbonitrile (400 mg), the mixture was stirred overnight at room temperature. Water was added to the reaction solution and the precipitated crystals were filtered off to obtain the title compound (480 mg) as light yellow crystals.

Workup

  1. filtrationthe precipitated crystals were filtered off

Sources & evidence

ORD record
ord-dfe32b034bae48fd865d74159346a7e2
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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