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

HRID 227701
Notes
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Reaction equation

HRID 227701 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 12661Diketene2×HCID 224802843-(4-fluorophenyl)-1H-indazol-5-amine

Product 1

HCID 86612339N-[3-(4-Fluorophenyl)-1H-indazol-5-yl]-3-oxobutanamideYield 44%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

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

  1. customthe reaction mixture was sealed
  2. customThe solvent was evaporated to dryness
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes