Acetoxyacetyl chloride → HCID 86675917, compound

HRID 572661Notes

Reaction equation

HRID 572661 reaction equation
Cl.[F:2][C:3]1[CH:30]=[CH:29][C:6]([CH2:7][NH:8][C:9]([C:11]2[CH:16]=[C:15]([C:17]3[CH2:21][CH:20]([CH:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)[O:19][N:18]=3)[N:14]=[C:13]([CH3:28])[N:12]=2)=[O:10])=[CH:5][C:4]=1[O:31][CH3:32].[C:33]([O:36][CH2:37][C:38](Cl)=[O:39])(=[O:35])[CH3:34]>ClCCl.O>[C:33]([O:36][CH2:37][C:38]([N:25]1[CH2:24][CH2:23][CH:22]([CH:20]2[O:19][N:18]=[C:17]([C:15]3[CH:16]=[C:11]([C:9](=[O:10])[NH:8][CH2:7][C:6]4[CH:29]=[CH:30][C:3]([F:2])=[C:4]([O:31][CH3:32])[CH:5]=4)[N:12]=[C:13]([CH3:28])[N:14]=3)[CH2:21]2)[CH2:27][CH2:26]1)=[O:39])(=[O:35])[CH3:34]

Participants

5

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 71466164HCID 71466164, compound

Product 1

HCID 86675917HCID 86675917, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a cold solution of N-(4-fluoro-3-methoxybenzyl)-2-methyl-6-(5-(piperidin-4-yl)-4,5-dihydroisoxazol-3-yl)pyrimidine-4-carboxamide hydrochloride (1.8 g, 3.87 mmol, Preparation #K.1) in dichloromethane (20 mL) were added TEA (3.3 mL, 23.2 mmol) and acetoxyacetyl chloride (0.5 mL, 4.65 mmol). The reaction mixture was slowly warmed to RT and stirred for about 10 min. The reaction mixture was diluted with water (10 mL) and the product was extracted with DCM (2×20 mL). The combined organic layers were washed with water (1×25 mL) followed by brine (1×50 mL). The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford 2-(4-(3-(6-(4-fluoro-3-methoxybenzylcarbamoyl)-2-methylpyrimidin-4-yl)-4,5-dihydroisoxazol-5-yl)piperidin-1-yl)-2-oxoethyl acetate as a brown solid 1.8 g (90%).

Workup

  1. extractionthe product was extracted with DCM (2×20 mL)
  2. washThe combined organic layers were washed with water (1×25 mL)
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c7a915ae12bf41aa8991dfdf854a59fd
Source dataset
uspto-grants-2015_05
Patent number
US09029409B2

Reaction notes

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