Ethyl orthoformate → HCID 67021616, compound

HRID 1660987Notes

Reaction equation

HRID 1660987 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16]3[C:21]([NH2:22])=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:12][CH:13]=2)[C:8](=[O:23])[CH2:7]1)=[O:5])[CH3:2].[CH:24](OCC)(OCC)OCC>>[CH2:1]([O:3][C:4]([CH:6]1[C:14]2[C:9](=[CH:10][C:11]([N:15]3[C:16]4=[N:17][CH:18]=[CH:19][CH:20]=[C:21]4[N:22]=[CH:24]3)=[CH:12][CH:13]=2)[C:8](=[O:23])[CH2:7]1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 131729210HCID 131729210, compound

Product 1

HCID 67021616HCID 67021616, compound

Procedure

A solution of (R/S)-5-(3-Amino-pyridin-2-ylamino)-3-oxo-indan-1-carboxylic acid ethyl ester (754 mg, 2.42 mmol) in triethyl orthoformate (25 mL) is heated at 145° C. for 30 min. The solvent is evaporated and the residue purified by flash chromatography eluting with Hexane/EtOAc. (R/S)-5-Imidazo[4,5-b]pyridine-3-yl-3-oxo-indan-1-carboxylic acid ethyl ester is obtained as a colourless solid. Title compound: 1H NMR: (DMSO-d6): 9.0 (s, 1H), 8.5 (d, 1H), 8.4 (d, 1H), 8.3 (s, 1H), 8.2 (d, 1H) 7.9 (d, 1H), 7.4 (dd, 1H) 4.5 (m, 1H), 4.2 (m, 2H), 3.0 (m, 2H), 1.2 (t, 3H); tR=1.2 min (System 2).

Workup

  1. customThe solvent is evaporated
  2. customthe residue purified by flash chromatography
  3. washeluting with Hexane/EtOAc

Sources & evidence

ORD record
ord-7f46d02ab3f04e4497d43b89ed8be3d2
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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