Ethyl orthoformate → HCID 67021375, compound

HRID 1660934Notes

Reaction equation

HRID 1660934 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[NH2:18])=[CH:7][CH:6]=1.[CH:20](OCC)(OCC)OCC>>[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:12]3[CH:17]=[CH:16][N:15]=[CH:14][C:13]=3[N:18]=[CH:20]2)=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 67021538HCID 67021538, compound

Product 1

HCID 67021375HCID 67021375, compound

Procedure

A mixture of [4-(3-amino-pyridin-4-ylamino)-phenyl]-acetic acid methyl ester (0.356 g, 1.39 mmol) and triethyl orthoformate (9.2 mL, 55.4 mmol, 40 equiv) is stirred and refluxed for 2 h. The resulting mixture is allowed to cool to rt and concentrated in vacuo to provide the title compound as a beige solid: ES-MS: 268.1 [M+H]+; single peak at tR=2.03 min (System 1).

Workup

  1. temperaturerefluxed for 2 h
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-01762cbc4cc0443cabbb27a120f31609
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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