4-(Pyrazin-2-yl)benzaldehyde → 3-{3-[(4-Pyrazin-2-yl-benzylamino)-methyl]-phenyl}-propionic acid methyl ester

HRID 2300460Notes

Reaction equation

HRID 2300460 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:15])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][NH2:14])[CH:8]=1.[N:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1>CO>[CH3:2][O:3][C:4](=[O:15])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][NH:14][CH2:26][C:25]2[CH:24]=[CH:23][C:22]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][N:16]=3)=[CH:29][CH:28]=2)[CH:8]=1

Participants

4

Reactant 2

HCID 38535194-(Pyrazin-2-yl)benzaldehydeHCID 22282736Methyl 3-(3-(aminomethyl)phenyl)propanoate hydrochloride

Product 1

HCID 541142043-{3-[(4-Pyrazin-2-yl-benzylamino)-methyl]-phenyl}-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound of Step A was prepared from 3-(3-aminomethyl-phenyl)-propionic acid methyl ester hydrochloride salt, of Preparation 44, and 4-pyrazin-2-yl-benzaldehyde, of Preparation 27, using the method described in Example 1, Step A except the imine was formed in MeOH at reflux over 2 h. 1H NMR (400 MHz, CDCl3) δ 9.02 (d, 1H), 8.61 (m, 1H), 8.48 (d, 1H), 7.98 (d, 2H), 7.49 (d, 2H), 7.25 (m, 1H), 7.19 (m, 2H), 7.09 (d,1H), 3.87 (s, 2H), 3.79 (s, 2H), 3.66 (s, 3H), 2.94 (t, 2H), 2.63 (t, 2H); MS 362 (M+1).

Workup

  1. temperatureat reflux over 2 h

Sources & evidence

ORD record
ord-ba7bd37fc4724645bd61f7e0bbbe9708
Source dataset
uspto-grants-2002_12
Patent number
US06498172B1

Reaction notes

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