4-(1,3-Thiazol-2-yl)benzaldehyde → 3-{3-[(4-Thiazol-2-yl-benzylamino)-methyl]-phenyl}-propionic acid methyl ester

HRID 2117482

Reaction equation

HRID 2117482 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.[S:16]1[CH:20]=[CH:19][N:18]=[C:17]1[C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=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]([C:17]3[S:16][CH:20]=[CH:19][N:18]=3)=[CH:28][CH:27]=2)[CH:8]=1

Participants

4

Reactant 2

HCID 105356554-(1,3-Thiazol-2-yl)benzaldehydeHCID 22282736Methyl 3-(3-(aminomethyl)phenyl)propanoate hydrochloride

Product 1

HCID 542857593-{3-[(4-Thiazol-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-thiazol-2-yl-benzaldehyde, of Preparation 25, 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 7.93 (d, 2H), 7.85 (d, 1H), 7.43 (d, 2H), 7.31 (d, 1H), 7.28-7.09 (m, 4H), 3.84 (s, 2H), 3.79 (s, 2H), 3.66 (s, 3H), 2.94 (t, 2H), 2.63 (t, 2H); MS 367 (M+1).

Workup

  1. temperatureat reflux over 2 h

Sources & evidence

ORD record
ord-ecd15424463c433493ba3798a20b5443
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Linked notes

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