Formamide → HCID 53326696, compound

HRID 2239503Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[N:12][C:11]=1[C:24]([O:26]CC)=O.C[N:30](C=O)C.C(N)=O.C[O-].[Na+]>CO.O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[N:12][C:11]=1[C:24]([NH2:30])=[O:26]

Participants

Conditions

Temperature: 100 °C

Procedure

To a 25 mL round bottom flask charged with a magnetic stir bar was added ethyl 4-[(2,4-difluorophenyl)amino]-6,7-dimethoxycinnoline-3-carboxylate (0.195 g, 0.50 mmol) (Method 27), anhydrous DMF (3 mL), formamide (0.135 g, 3 mmol), and 3 mL of a 0.5 M solution of sodium methoxide in MeOH. The reaction was warmed to 100° C. for 2 h before being allowed to cool to rt. The reaction was poured over water (˜50 mL) and the crude product precipitated from solution. The solid was collected via vacuum filtration using a Buchner funnel and was purified on 40 g silica using EtOAc/MeOH (4:1) as eluent providing 0.174 g (96%) of the title compound as a white solid. 1H NMR: 11.35 (s, 1H), 8.86 (s, 1H), 8.05 (s, 1H), 7.71 (s, 1H), 7.48 (m, 1H), 7.38 (m, 1H), 7.18 (m, 1H), 6.69 (s, 1H), 4.06 (s, 3H), 3.50 (s, 3H); m/z 361.

Workup

additionTo a 25 mL round bottom flask charged with a magnetic stir bar
temperatureto cool to rt
customthe crude product precipitated from solution
filtrationThe solid was collected via vacuum filtration
customwas purified on 40 g silica

Sources & evidence

ORD record: ord-a0edac84eb5248d1829919abbe6a98e0
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723337B2

Reaction notes

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