Ammonia → HCID 59377844, compound

HRID 1691819Notes

Reaction equation

HRID 1691819 reaction equation
[Br:1][C:2]1[C:3]([NH:13][C:14]([N:16]2[CH:21]=[CH:20][C:19](=[O:22])[CH2:18][C@H:17]2[C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[O:15])=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7](O)=[O:8].C[N:31](C)C=O.C(Cl)(=O)C(Cl)=O.N>ClCCl.O1CCOCC1>[Br:1][C:2]1[C:3]([NH:13][C:14]([N:16]2[CH:21]=[CH:20][C:19](=[O:22])[CH2:18][C@H:17]2[C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[O:15])=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([NH2:31])=[O:8]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 59377724HCID 59377724, compound

Product 1

HCID 59377844HCID 59377844, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

(S)-5-Bromo-4-{[2-(4-fluoro-phenyl)-4-oxo-3,4-dihydro-2H-pyridine-1-carbonyl]-amino}-2-methoxy-benzoic acid (72 mg) was dissolved in 2 ml dichloromethane and 0.001 ml dimethylformamide under argon. To this solution was added 0.02 ml oxalyl chloride and the solution was stirred for three hours. The solution was then slowly added at 0° C. to 0.5M NH3 in dioxane. After stirring for 10 minutes, the mixture was concentrated in vacuo and chromatographed (dichloromethane) to yield 26 mg (S)-5-bromo-4-{[2-(4-fluoro-phenyl)-4-oxo-3,4-dihydro-2H-pyridine-1-carbonyl]-amino}-2-methoxy-benzamide. MS (M+H) 463.

Workup

  1. stirringAfter stirring for 10 minutes
  2. concentrationthe mixture was concentrated in vacuo
  3. customchromatographed (dichloromethane)

Sources & evidence

ORD record
ord-67fa7712f1d24ffb8295aa99784bf3b1
Source dataset
uspto-grants-2012_04
Patent number
US08153809B2

Reaction notes

Loading…