Diketene → N-[3-(4-Fluorophenyl)-1H-indazol-5-yl]-3-oxobutanamide

HRID 227701Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH2:17])[CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1.[CH2:18]=[C:19]1[O:23][C:21](=[O:22])[CH2:20]1>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:21](=[O:22])[CH2:20][C:19](=[O:23])[CH3:18])[CH:15]=3)[NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

The product of Step (d) (0.5 g, 2.2 mmol) was dissolved in acetonitrile (1 ml). In a separate flask, diketene (0.17 ml, 2.2 mmol, stabilized with copper sulfate) was dissolved in acetonitrile (1 ml). The diketene solution was added to the amine suspension In three portions, the reaction mixture was sealed and heated to 50° C. for 18 hours. The solvent was evaporated to dryness and purified by silica gel chromatography (5% MeOH/CH2Cl2) to afford the title compound, (0.3 g, 44%); MS (ES+) m/e 313 [M+H]+.

Workup

customthe reaction mixture was sealed
customThe solvent was evaporated to dryness
custompurified by silica gel chromatography (5% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-38ebe72b4eb4433197b64cae09c16758
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560467B2

Reaction notes

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