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

HRID 1010339Notes

Reaction equation

HRID 1010339 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-549eaf73fbd54e92bb10f789f5faf98d
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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