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 587607Notes

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].[Cl-].[Cl-].[Ca+2].[C:35]([O:38]C(=O)C)(=[O:37])[CH3:36]>>[C:35]([O:38][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:37])[CH3:36]

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 5284359Calcium Chloride

HCID 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

Procedure

The 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 (500 mg) in acetic anhydride (10 mL) was stirred at 80° C. under a dry atmosphere (CaCl2 tube) for 2 h. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 0%-30% EtOAc in hexane) to give [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 (300 mg) as colorless oil.

Workup

concentrationThe reaction mixture was concentrated in vacuo
customThe residue was purified by column chromatography (silica gel, eluted with 0%-30% EtOAc in hexane)

Sources & evidence

ORD record: ord-6b0b062f45ed4bf3a1de12cfb0f0616e
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226921B2

Reaction notes

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