Acetoxyacetyl chloride → 2-{[6-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-(2-hydroxy-2-methylpropanoyl)furo[2,3-b]pyridin-3yl]amino}-2-oxoethyl acetate

HRID 8815Notes

Reaction equation

HRID 8815 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)[CH:9]=2)[O:4][C:3]=1[C:25](=[O:30])[C:26]([OH:29])([CH3:28])[CH3:27].[C:31]([O:34][CH2:35][C:36](Cl)=[O:37])(=[O:33])[CH3:32]>C(#N)C.C(Cl)Cl>[C:31]([O:34][CH2:35][C:36]([NH:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)[CH:9]=2)[O:4][C:3]=1[C:25](=[O:30])[C:26]([OH:29])([CH3:27])[CH3:28])=[O:37])(=[O:33])[CH3:32]

Participants

5

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 103660061-(3-Amino-6-(2-chlorophenyl)-5-(4-chlorophenyl)furo[2,3-b]pyridin-2-yl)-2-hydroxy-2-methylpropan-1-one

Product 1

HCID 219849132-{[6-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-(2-hydroxy-2-methylpropanoyl)furo[2,3-b]pyridin-3yl]amino}-2-oxoethyl acetate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4.0 g of the product of Example 100 in 25 mL of acetonitrile was added 7.5 mL acetoxy acetylchloride and the reaction mixture was stirred at room temperature. After 50 min the reaction mixture was diluted with CH2Cl2 and washed two times with aqueous sodium bicarbonate. The organic layer was dried over sodium sulfate then concentrated. The residue was suspended in 150 mL of methanol at 60–65° C. After cooling to room temperature the methanol was decanted away and the solid rinsed three times with fresh methanol. The solids were then dried in vacuo to afford the title compound. HPLC/MS: 540.9 (M+1), 542.8 (M+3); Rt=4.07 min.

Workup

  1. washwashed two times with aqueous sodium bicarbonate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationthen concentrated
  4. customwas suspended in 150 mL of methanol at 60–65° C
  5. temperatureAfter cooling to room temperature the methanol
  6. customwas decanted away
  7. washthe solid rinsed three times with fresh methanol
  8. customThe solids were then dried in vacuo

Sources & evidence

ORD record
ord-d705a74c03e9403c99b2e96def32a4aa
Source dataset
uspto-grants-2006_08
Patent number
US07091216B2

Reaction notes

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