Acetyl chloride → HCID 67215711, compound

HRID 472910Notes

Reaction equation

HRID 472910 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:10])[CH3:9].Cl.[NH2:13][C:14]1[CH:15]=[CH:16][C:17]2[N:18]([C:20]([C:23]([C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[C:27]([O:34][CH3:35])[CH:26]=3)=[O:24])=[N:21][CH:22]=2)[CH:19]=1.C(=O)(O)[O-].[Na+]>ClCCCl.O>[CH3:35][O:34][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][C:28]=1[N+:31]([O-:33])=[O:32])[C:23]([C:20]1[N:18]2[CH:19]=[C:14]([NH:13][C:8](=[O:10])[CH3:9])[CH:15]=[CH:16][C:17]2=[CH:22][N:21]=1)=[O:24]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 67216202HCID 67216202, compound

Product 1

HCID 67215711HCID 67215711, compoundYield 62.4%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

1.29 ml (9.29 mmol) of triethylamine and then 0.51 ml (7.15 mmol) of acetyl chloride are added to 0.50 g (1.43 mmol) of (6-aminoimidazo[1,5-a]pyridin-3-yl)(3-methoxy-4-nitrophenyl)methanone hydrochloride in 25 ml of 1,2-dichloroethane cooled to 5° C. and then the mixture is allowed to return to ambient temperature and is stirred for 18 hours. The medium is taken up in water, basified with a sodium bicarbonate solution and extracted with dichloromethane. The organic phase is washed with a saturated aqueous sodium chloride solution, then dried over sodium sulfate and concentrated under reduced pressure. The product is purified by column chromatography on silica gel, elution being carried out with a mixture of dichloromethane and acetone (90/10). 316 mg of a yellow solid are obtained. Melting point: 257° C.; 1H NMR (d6-DMSO): 2.15 (3H, s), 4.01 (3H, s), 7.45 (1H, d), 7.92 (1H, s), 8.00-8.06 (3H, m), 8.13 (1H, s), 10.62 (1H, s)

Workup

  1. customto return to ambient temperature
  2. extractionextracted with dichloromethane
  3. washThe organic phase is washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe product is purified by column chromatography on silica gel, elution
  7. additionbeing carried out with a mixture of dichloromethane and acetone (90/10)

Sources & evidence

ORD record
ord-c2d74700ce7141aa9146096af5256090
Source dataset
uspto-grants-2014_01
Patent number
US08633216B2

Reaction notes

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