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Ammonia → HCID 67361982, compound

HRID 1183188
Notes
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Reaction equation

HRID 1183188 reaction equation
C(Cl)(=O)C(Cl)=O.[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[C:18]([O:19][CH3:20])=[CH:17][C:16]([C:21]([NH:23][C@H:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])[CH2:25][C:26]([OH:28])=O)=[O:22])=[N:15]1.[NH3:36]>C(Cl)Cl.CN(C=O)C>[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[C:18]([O:19][CH3:20])=[CH:17][C:16]([C:21]([NH:23][C@H:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])[CH2:25][C:26]([NH2:36])=[O:28])=[O:22])=[N:15]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 533087431279038-40-2

Product 1

HCID 67361982HCID 67361982, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344
Dichloromethane
Solvent

Procedure

DMF (1.8 mg, 25 μmol) and oxalyl chloride (160 mg, 1.26 mmol) were added to a solution of (S)-3-{[1-(2-fluoro-phenyl)-5-methoxy-1H-pyrazole-3-carbonyl]-amino}-3-(2-methyl-phenyl)-propionic acid (500 mg, 1.26 mmol) in DCM (5 ml) at room temperature. After 16 h at room temperature a 33% aqueous solution of ammonia (649 mg, 12.6 mmol) was added and the mixture was stirred for further 16 h. The solvent was removed under reduced pressure and the residue was purified by preparative HPLC to give 170 mg (34%) of the title compound as a colorless oil.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-7d4ed9180d8f4ca9adb9b2252c175952
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08664257B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes