2-chloro-N-(4-fluorophenyl)acetamide → N-(4-Fluorophenyl)-N2-[3-methoxy-4-(5-oxazolyl)phenyl]glycinamide

HRID 1168428Notes

Reaction equation

HRID 1168428 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][CH:11]=[N:10][CH:9]=2)=[C:4]([O:13][CH3:14])[CH:3]=1.Cl[CH2:16][C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)=[O:18]>CN(C=O)C>[F:26][C:23]1[CH:22]=[CH:21][C:20]([NH:19][C:17](=[O:18])[CH2:16][NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[O:12][CH:11]=[N:10][CH:9]=3)=[C:4]([O:13][CH3:14])[CH:3]=2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 5320652-chloro-N-(4-fluorophenyl)acetamideHCID 154627323-Methoxy-4-(oxazol-5-yl)aniline

Product 1

HCID 9862808N-(4-Fluorophenyl)-N2-[3-methoxy-4-(5-oxazolyl)phenyl]glycinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1D, (101 mg, 0.53 mmol) and 2-chloro-4′-fluoroacetanilide (50 mg, 0.27 mmol) in DMF (0.15 mL) was heated at 100° C. for 15 h. After the reaction had cooled, the solvent was removed under reduced pressure, and the residue was subjected to preparative HPLC to give 1 as a tan solid. LC/MS: ret. timeA32 3.527 min., MS (M+H)+=342.

Workup

  1. temperatureAfter the reaction had cooled
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2fc9946af56c47d69d4b5e7973b349ac
Source dataset
uspto-grants-2003_09
Patent number
US06624184B1

Reaction notes

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