Ethyl orthoformate → HCID 67021389, compound

HRID 1661024Notes

Reaction equation

HRID 1661024 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:17]([NH2:18])=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:7][C:6]=1[CH3:19].[CH:21](OCC)(OCC)OCC>>[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:17]3[N:18]=[CH:21]2)=[CH:7][C:6]=1[CH3:19]

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 67021599HCID 67021599, compound

Product 1

HCID 67021389HCID 67021389, compound

Conditions

Temperature
150 °C

Procedure

A mixture of [4-(3-amino-pyridin-2-ylamino)-2-methyl-phenyl]-acetic acid methyl ester (1.92 g, 7.08 mmol) and triethyl orthoformate (30 mL, 181 mmol, 26 equiv) is stirred for 3 h at 150° C. The resulting mixture is allowed to cool to rt and concentrated in vacuo to provide the title compound: ES-MS: 282.1 [M+H]+; tR=3.39 min (System 1).

Workup

  1. temperatureto cool to rt
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4555782609834ccdb420e0b28d5a278a
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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