N-(3-methoxyphenyl)piperazine → Methyl {2-[4-(3-methoxyphenyl)piperazin-1-yl]-3-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrido[3,4-d]pyrimidin-4-yl}acetate

HRID 1443812Notes

Reaction equation

HRID 1443812 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([N:9]=[C:10]=[N:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][C:17]=2/[CH:18]=[CH:19]/[C:20]([O:22][CH3:23])=[O:21])[CH:6]=[CH:7][CH:8]=1.[CH3:26][O:27][C:28]1[CH:29]=[C:30]([N:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[CH:31]=[CH:32][CH:33]=1>>[CH3:26][O:27][C:28]1[CH:29]=[C:30]([N:34]2[CH2:39][CH2:38][N:37]([C:10]3[N:9]([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:24])([F:1])[F:25])[CH:4]=4)[CH:18]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:17]4[CH:16]=[CH:15][N:14]=[CH:13][C:12]=4[N:11]=3)[CH2:36][CH2:35]2)[CH:31]=[CH:32][CH:33]=1

Participants

3

Reactant 2

HCID 81430N-(3-methoxyphenyl)piperazineHCID 86620420Methyl (2E)-3-{3-[({[3-(trifluoromethyl)phenyl]imino}methylene)amino]pyridin-4-yl}acrylate

Product 1

HCID 59168068Methyl {2-[4-(3-methoxyphenyl)piperazin-1-yl]-3-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrido[3,4-d]pyrimidin-4-yl}acetate

Procedure

Starting from 250 mg (0.34 mmol) of the carbodiimide from Example 17A and 69 mg (0.36 mmol) of 3-methoxyphenylpiperazine, general procedure [C] and purification by preparative HPLC result in 90 mg (46% of theory) of product.

Workup

  1. customresult in 90 mg (46% of theory) of product

Sources & evidence

ORD record
ord-f3202e2cc82f4dfbb55d5592c78a9e0b
Source dataset
uspto-grants-2010_02
Patent number
US07662822B2

Reaction notes

Loading…