Dimethylacetamide → Methyl 7-(2-fluoro-4-iodophenylamino)-8-fluoro-4-methylquinazoline-6-carboxylate

HRID 1161835Notes

Reaction equation

[C:1]([C:4]1[C:5](F)=[C:6]([F:23])[C:7]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=2[F:22])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])(=O)[CH3:2].C(O)(=O)C.[CH:29]([NH2:31])=O.CC([N:35](C)C)=O>CCOC(C)=O>[F:22][C:16]1[CH:17]=[C:18]([I:21])[CH:19]=[CH:20][C:15]=1[NH:14][C:7]1[C:6]([F:23])=[C:5]2[C:4]([C:1]([CH3:2])=[N:35][CH:29]=[N:31]2)=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of methyl 5-acetyl-2-(2-fluoro-4-iodophenylamino)-3,4-difluorobenzoate (230 mg, 0.55 mmol) and formamide acetate (68 mg, 0.66 mmol) in DMA (5 ml) was heated at 95° C. for 6 hours. The reaction mixture was diluted with EtOAc and washed with water and brine. The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford 205 mg (88%) of the title compound.

Workup

washwashed with water and brine
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-aee93ad456844041956282cd1adf072d
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820664B2

Reaction notes

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