Triethyl orthoacetate → HCID 22238151, compound

HRID 2117339Notes

Reaction equation

HRID 2117339 reaction equation
[C:1](OCC)(OCC)(OCC)[CH3:2].[C:12]([NH:20][C:21]1[CH:22]=[CH:23][C:24]([Cl:39])=[C:25]([NH:27][C:28](=[O:38])[C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:30]=2[NH2:37])[CH:26]=1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[C:12]([NH:20][C:21]1[CH:22]=[CH:23][C:24]([Cl:39])=[C:25]([N:27]2[C:28](=[O:38])[C:29]3[C:30](=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=3)[N:37]=[C:1]2[CH3:2])[CH:26]=1)(=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 66221Triethyl orthoacetateHCID 9908705N-(5-benzamido-2-chlorophenyl)-2-amino-4-methoxybenzamide

Product 1

HCID 22238151HCID 22238151, compoundYield 27%

Procedure

Using an analogous procedure to that described in Example 1, triethyl orthoacetate was reacted with N-(5-benzamido-2-chlorophenyl)-2-amino-4-methoxybenzamide. The material so obtained was purified by column chromatography on an isolute SCX ion exchange column using initially methanol and then a 99:1 mixture of methanol and a saturated aqueous ammonium hydroxide solution as eluent. There was thus obtained the title compound in 27% yield; NMR Spectrum: (DMSOd6) 2.15 (s, 3H), 3.91 (s, 3H), 7.09-7.14 (m, 2H), 7.46-7.6 (m, 3H), 7.71 (d, 1H), 7.87-8.06 (m, 5H), 10.57 (s, 1H); Mass Spectrum: M+H+ 420 and 422.

Workup

  1. customThe material so obtained
  2. customwas purified by column chromatography on an isolute SCX ion exchange column
  3. additiona 99:1 mixture of methanol

Sources & evidence

ORD record
ord-c95786ca6cff4245946fb77036000444
Source dataset
uspto-grants-2008_10
Patent number
US07442704B2

Reaction notes

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