4-(1H-Pyrazol-1-yl)benzaldehyde → 3-{3-[(4-Pyrazol-1-yl-benzylamino)-methyl]-phenyl}-propionic acid methyl ester

HRID 2117487

Reaction equation

HRID 2117487 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([C:21]2[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=2)[CH:20]=[CH:19][CH:18]=[N:17]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][CH2:25][C:24]2[CH:23]=[CH:22][C:21]([N:16]3[CH:20]=[CH:19][CH:18]=[N:17]3)=[CH:28][CH:27]=2)[CH:8]=1

Participants

4

Reactant 2

HCID 27764774-(1H-Pyrazol-1-yl)benzaldehydeHCID 22282736Methyl 3-(3-(aminomethyl)phenyl)propanoate hydrochloride

Product 1

HCID 540597813-{3-[(4-Pyrazol-1-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-pyrazol-1-yl-benzaldehyde, of Preparation 42, 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 7.81 (s, 1H), 7.44 (d, 2H), 7.32 (d, 2H), 7.24 (m, 2H), 7.17 (m, 3H), 7.07 (d, 1H), 3.82 (s, 2H), 3.77 (s, 2H), 3.64 (s, 3H), 2.92 (t, 2H), 2.61 (t, 2H); MS 350 (M+1).

Workup

  1. temperatureat reflux over 2 h

Sources & evidence

ORD record
ord-1579193c9392446bb7b0cc8fe87d84f0
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Linked notes

Loading…