Acetyl chloride → HCID 67215434, compound

HRID 472919Notes

Reaction equation

HRID 472919 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:10])[CH3:9].[NH2:12][C:13]1[N:14]=[C:15]([C:22]([C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[C:26]([O:33][CH3:34])[CH:25]=2)=[O:23])[N:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=12>ClCCCl.ClCCl.O>[CH3:34][O:33][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][C:27]=1[N+:30]([O-:32])=[O:31])[C:22]([C:15]1[N:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]2=[C:13]([NH:12][C:8](=[O:10])[CH3:9])[N:14]=1)=[O:23]

Participants

7

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 67215846(1-Aminoimidazo[1,5-a]pyridin-3-yl)(3-methoxy-4-nitrophenyl)methanone

Product 1

HCID 67215434HCID 67215434, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

0.54 ml (3.84 mmol) of triethylamine and then 0.21 ml (2.95 mmol) of acetyl chloride are added, under a nitrogen atmosphere, to 0.8 g (2.56 mmol) of (1-aminoimidazo[1,5-a]pyridin-3-yl)(3-methoxy-4-nitro-phenyl)methanone obtained in example 76 in 20 ml of 1,2-dichloroethane. The reaction medium is stirred at ambient temperature for 16 hours and then taken up in a mixture of dichloromethane and water. The organic phase is separated by settling, dried over sodium sulfate and concentrated under reduced pressure. The residue obtained is purified by column chromatography on silica gel, elution being carried out with a dichloromethane/acetone (94/6) mixture. 0.523 g of an orange solid is collected. Melting point: 256° C.; 1H NMR (d6-DMSO): 2.14 (3H, s), 4.02 (3H, s), 7.34-7.44 (2H, m), 7.94-8.08 (3H, m), 8.09 (1H, s), 9.75 (1H, d)

Workup

  1. customThe organic phase is separated
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue obtained
  5. customis purified by column chromatography on silica gel, elution
  6. custom0.523 g of an orange solid is collected

Sources & evidence

ORD record
ord-488e3eae7e1a4744b8eb9ea34366e2c9
Source dataset
uspto-grants-2014_01
Patent number
US08633216B2

Reaction notes

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