m-Aminoacetanilide → N-{3-[1-(2-fluoro-4-iodophenyl)-3-(4-methoxybenzyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidin-5-ylamino]-phenyl}-acetamide

HRID 75676

Reaction equation

HRID 75676 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14]2[N:15]([CH3:29])[C:16](=[O:28])[C:17]([CH3:27])=[C:18](OS(C(F)(F)F)(=O)=O)[C:13]=2[C:12](=[O:30])[N:11]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)[C:10]1=[O:40].[NH2:41][C:42]1[CH:43]=[C:44]([CH:49]=[CH:50][CH:51]=1)[NH:45][C:46](=[O:48])[CH3:47].CN(C)C(=O)C.N1C(C)=CC=CC=1C>CO>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14]2[N:15]([CH3:29])[C:16](=[O:28])[C:17]([CH3:27])=[C:18]([NH:41][C:42]3[CH:43]=[C:44]([NH:45][C:46](=[O:48])[CH3:47])[CH:49]=[CH:50][CH:51]=3)[C:13]=2[C:12](=[O:30])[N:11]([CH2:31][C:32]2[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=2)[C:10]1=[O:40]

Participants

6

Reactant 4

HCID 7604m-AminoacetanilideHCID 79372,6-LutidineHCID 31374DimethylacetamideHCID 59717176Trifluoromethanesulfonic acid 1-(2-fluoro-4-iodophenyl)-3-(4-methoxybenzyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidin-5-yl ester

Product 1

HCID 59717402N-{3-[1-(2-fluoro-4-iodophenyl)-3-(4-methoxybenzyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidin-5-ylamino]-phenyl}-acetamideYield 94.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To trifluoromethanesulfonic acid 1-(2-fluoro-4-iodophenyl)-3-(4-methoxybenzyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidin-5-yl ester 86 (1.10 g) and 3′-aminoacetanilide 57 (285 mg) were added, N,N-dimethylacetamide (2.20 ml) and 2,6-lutidine (221 μl), and the mixture was stirred at 130° C. for 2 hrs. After allowing to return to room temperature, methanol (12.0 ml) was added dropwise with stirring. The precipitated crystals were collected by filtration, washed with methanol and dried to give N-{3-[1-(2-fluoro-4-iodophenyl)-3-(4-methoxybenzyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidin-5-ylamino]-phenyl}-acetamide 87 (1.04 g, yield 94.6%) as colorless crystals.

Workup

  1. customto return to room temperature
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed with methanol
  4. customdried

Sources & evidence

ORD record
ord-bf230acaec014a2da740100836d07af8
Source dataset
uspto-grants-2014_09
Patent number
US08835443B2

Linked notes

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