Acetic Anhydride → [1-ethyl-2-oxo-3-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yl]methyl acetate

HRID 587613Notes

Reaction equation

HRID 587613 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[N+:7]([O-])[CH:8]=[CH:9][C:10]=2[CH3:12])[N:5]([C:14]2[CH:19]=[CH:18][C:17]([O:20][Si:21]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])=[CH:16][CH:15]=2)[C:4]1=[O:31])[CH3:2].[CH3:32][C:33]([O:35]C(C)=O)=[O:34]>>[C:33]([O:35][CH2:12][C:10]1[CH:9]=[CH:8][N:7]=[C:6]2[N:5]([C:14]3[CH:15]=[CH:16][C:17]([O:20][Si:21]([CH:22]([CH3:23])[CH3:24])([CH:25]([CH3:26])[CH3:27])[CH:28]([CH3:30])[CH3:29])=[CH:18][CH:19]=3)[C:4](=[O:31])[N:3]([CH2:1][CH3:2])[C:11]=12)(=[O:34])[CH3:32]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 585774851-ethyl-7-methyl-3-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one 4-oxide

Product 1

HCID 58577611[1-ethyl-2-oxo-3-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yl]methyl acetate

Conditions

Temperature
80 °C

Procedure

A mixture of 1-ethyl-7-methyl-3-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one 4-oxide (1 g) and Ac2O (20 mL) was stirred at 80° C. for 2 h, and concentrated in vacuo. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (0.49 g).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-5436a3b84e1c4b1087b028f8fbdf911d
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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