Ethyl orthoformate → HCID 67021415, compound

HRID 1660981Notes

Reaction equation

HRID 1660981 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[C:19]([NH2:20])=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH:9][CH:8]=1)=[O:6])[CH3:2].[CH:22](OCC)(OCC)OCC>>[CH2:1]([O:3][C:4](=[O:21])[C:5]([C:7]1[CH:8]=[CH:9][C:10]([N:13]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:19]3[N:20]=[CH:22]2)=[CH:11][CH:12]=1)=[O:6])[CH3:2]

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 67021578HCID 67021578, compound

Product 1

HCID 67021415HCID 67021415, compound

Procedure

A solution of [4-(3-amino-pyridin-2-ylamino)-phenyl]oxo-acetic acid ethyl ester (195 mg, 0.547 mmol) in triethyl orthoformate (5 mL) is heated at 144° C. for 5 h. The reaction mixture is left in the fridge over night and then refluxed for additional 5 h. The solvent is removed and the product is purified by reverse phase MPLC with ACN/water to afford (4-imidazo[4,5-b]pyridine-3-yl-phenyl)-oxo-acetic acid ethyl ester. ES-MS: 296.10 [M+H]+; tR=1.4 min (System 2).

Workup

  1. waitThe reaction mixture is left in the fridge over night
  2. temperaturerefluxed for additional 5 h
  3. customThe solvent is removed
  4. customthe product is purified by reverse phase MPLC with ACN/water

Sources & evidence

ORD record
ord-98746c77739e4ea1a1e9855a2aac5dec
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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