Ethyl orthoformate → HCID 67021592, compound

HRID 1661015Notes

Reaction equation

HRID 1661015 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[C:10]([Cl:11])=[CH:9][C:8]([NH:12][C:13]2[C:18]([NH2:19])=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:7][C:6]=1[Cl:20].[CH:22](OCC)(OCC)OCC>>[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[C:10]([Cl:11])=[CH:9][C:8]([N:12]2[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:18]3[N:19]=[CH:22]2)=[CH:7][C:6]=1[Cl:20]

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 67021584HCID 67021584, compound

Product 1

HCID 67021592HCID 67021592, compound

Procedure

A mixture of [4-(3-amino-pyridin-2-ylamino)-2,6-dichloro-phenyl]-acetic acid methyl ester (4.5 g, 13.8 mmol) and triethyl orthoformate (60 mL, 361 mmol, 26 equiv) is stirred for 13.5 h at reflux. The resulting mixture is allowed to cool to rt and concentrated in vacuo to provide the title compound as a dark solid: ES-MS: 336.0/338.0 [M+H]+; tR=4.58 min (System 1); Rf=0.28 (Hexane/EtOAc, 1:1).

Workup

  1. temperatureat reflux
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-87d8663f717a4254affdc992695a7e4c
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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