4-Methoxyphenylacetyl chloride → HCID 23498798, compound

HRID 1836115Notes

Reaction equation

HRID 1836115 reaction equation
[NH2:1][C:2]1[C:3]([CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:4][O:5][C:6]=1[C:7]([NH2:9])=[O:8].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24](Cl)=[O:25])=[CH:19][CH:18]=1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH:10]1([C:3]2[C:2]([NH:1][C:24](=[O:25])[CH2:23][C:20]3[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=3)=[C:6]([C:7]([NH2:9])=[O:8])[O:5][N:4]=2)[CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

5

Reactant 2

HCID 27346884-Methoxyphenylacetyl chlorideHCID 23498803HCID 23498803, compound

Product 1

HCID 23498798HCID 23498798, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

12 g (61 mmol) of 4-amino-3-cyclopentyl-isoxazole-5-carboxamide (example VI) are dissolved in 50 ml of pyridine, and 12.48 g (67 mmol) of 4-methoxyphenylacetyl chloride and a spatula tip of DMAP are added. The reaction mixture is stirred at 60° C. for 5 hours and the solvent is then removed in vacuo. The residue is taken up in dichloromethane and the solution is shaken twice with 1N hydrochloric acid and twice with sodium hydrogencarbonate solution; it is then dried over sodium sulfate and the solvent is removed in vacuo. The residue is triturated with a little dichloromethane and then filtered; the filtrate is concentrated to dryness and the residue is purified by chromatography (cyclohexane/ethyl acetate=2:1).

Workup

  1. customthe solvent is then removed in vacuo
  2. stirringthe solution is shaken twice with 1N hydrochloric acid and twice with sodium hydrogencarbonate solution
  3. dry with materialit is then dried over sodium sulfate
  4. customthe solvent is removed in vacuo
  5. customThe residue is triturated with a little dichloromethane
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated to dryness
  8. customthe residue is purified by chromatography (cyclohexane/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-0316edfe356d49b7ba0d242974711a08
Source dataset
uspto-grants-2004_08
Patent number
US06777416B2

Reaction notes

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