Acetic Anhydride → [[[5-[(2,5-Difluorophenyl)(4-fluorophenylsulfonyl)methyl]-4-methylpyridin-2-yl]carbonyl]amino]methyl Acetate

HRID 1641732Notes

Reaction equation

HRID 1641732 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]([S:22]([C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)(=[O:24])=[O:23])[C:10]1[C:11]([CH3:21])=[CH:12][C:13]([C:16]([NH:18][CH2:19][OH:20])=[O:17])=[N:14][CH:15]=1.[C:32](OC(=O)C)(=[O:34])[CH3:33]>N1C=CC=CC=1>[C:32]([O:20][CH2:19][NH:18][C:16]([C:13]1[CH:12]=[C:11]([CH3:21])[C:10]([CH:9]([C:3]2[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=2[F:1])[S:22]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)(=[O:24])=[O:23])=[CH:15][N:14]=1)=[O:17])(=[O:34])[CH3:33]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 119996905-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-N-(1-hydroxymethyl)-4-methylpyridine-2-carboxamide

Product 1

HCID 57736465[[[5-[(2,5-Difluorophenyl)(4-fluorophenylsulfonyl)methyl]-4-methylpyridin-2-yl]carbonyl]amino]methyl AcetateYield 39%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-N-(1-hydroxymethyl)-4-methylpyridine-2-carboxamide (200 mg, 0.44 mmol) obtained in Example 85 in pyridine (2 ml), acetic anhydride (2 ml) was added, and the mixture was stirred for 3 hours at room temperature. The reaction mixture was concentrated under reduced pressure, and then the residue was dissolved in ethyl acetate, and was washed with water. The solution was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography. The fraction obtained from an elution with hexane:ethyl acetate=10:3 was concentrated under reduced pressure, washed with diethyl ether, and was collected by filtration, to obtain the title compound (86 mg, 0.17 mmol, 39%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwas washed with water
  4. dry with materialThe solution was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe fraction obtained from an elution with hexane
  8. concentrationethyl acetate=10:3 was concentrated under reduced pressure
  9. washwashed with diethyl ether
  10. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-16d3f35920be4f8d9433c98f9cd0b32c
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

Loading…