Acetic Anhydride → N-(6-(2-chlorophenyl)-5-(4-chlorophenyl)-2-(2-hydroxy-2-methylpropanoyl)furo[2,3-b]pyridin-3-yl)acetamide

HRID 8817Notes

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](OC(=O)C)(=[O:33])[CH3:32]>C(O)(=O)C>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:7]1[N:6]=[C:5]2[O:4][C:3]([C:25](=[O:30])[C:26]([OH:29])([CH3:27])[CH3:28])=[C:2]([NH:1][C:31](=[O:33])[CH3:32])[C:10]2=[CH:9][C:8]=1[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 85 °C

Procedure

The product of Example 100 (0.200 g), acetic anhydride (1.25 mL) and acetic acid (0.25 mL) were combined and then heated to 85° C. After 3 h the reaction was concentrated and the residue was dissolved in dichloromethane and washed twice with aqueous sodium bicarbonate. The solution was then concentrated and the residue was purified via flash chromatography on silica gel with gradient elution of 0–60% ethyl acetate in hexanes affording the title compound. HPLC/MS: 483.0 (M+1), 484.8 (M+3); Rt=3.95-min.

Workup

concentrationAfter 3 h the reaction was concentrated
dissolutionthe residue was dissolved in dichloromethane
washwashed twice with aqueous sodium bicarbonate
concentrationThe solution was then concentrated
customthe residue was purified via flash chromatography on silica gel with gradient elution of 0–60% ethyl acetate in hexanes affording the title compound

Sources & evidence

ORD record: ord-e1aac933471c4119887b78fda5452eab
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091216B2

Reaction notes

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