4-Chlorobenzylamine → N-(4-Chlorobenzyl)-4-methyl-2-(morpholin-4-ylmethyl)-7-oxo-4,7-dihydro[1,3]-thiazolo[5,4-b]pyridine-6-carboxamide

HRID 411213Notes

Reaction equation

HRID 411213 reaction equation
[CH3:1][N:2]1[CH:7]=[C:6]([C:8](OCC)=[O:9])[C:5](=[O:13])[C:4]2[N:14]=[C:15]([CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[S:16][C:3]1=2.[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1>>[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH:30][C:8]([C:6]2[C:5](=[O:13])[C:4]3[N:14]=[C:15]([CH2:17][N:18]4[CH2:19][CH2:20][O:21][CH2:22][CH2:23]4)[S:16][C:3]=3[N:2]([CH3:1])[CH:7]=2)=[O:9])=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 660364-ChlorobenzylamineHCID 22397170Ethyl 4-Methyl-2-(morpholin-4-ylmethyl)-7-oxo-4,7-dihydro[1,3]thiazolo[5,4-b]pyridine-6-carboxylate

Product 1

HCID 22397158N-(4-Chlorobenzyl)-4-methyl-2-(morpholin-4-ylmethyl)-7-oxo-4,7-dihydro[1,3]-thiazolo[5,4-b]pyridine-6-carboxamide

Conditions

Temperature
190 °C

Procedure

A mixture of ethyl 4-methyl-2-(morpholin-4-ylmethyl)-7-oxo-4,7-dihydro[1,3]-thiazolo[5,4-b]pyridine-6-carboxylate (Preparation 30, 105 mg) and 4-chlorobenzyl-amine (1 mL) is heated to 190° C. for 40 min. and then allowed to cool to ambient temperature. The solvent is removed in vacuo. The mixture is diluted with ether to precipitate 89 mg (66%) of the title compound as a tan solid. Physical characteristics: 1H NMR (DMSO-d6) δ 2.59, 3.64, 3.91, 4.00, 4.56, 7.33-7.36, 8.75, 10.59; IR (diffuse reflectance) 2857, 2809, 1662, 1599, 1569, 1550, 1531, 1526, 1517, 1492, 1346, 1296, 1116, 797, 732 cm−1. Anal. Found: C, 55.50; H, 4.98; N, 12.00.

Workup

  1. temperatureto cool to ambient temperature
  2. customThe solvent is removed in vacuo
  3. additionThe mixture is diluted with ether
  4. customto precipitate 89 mg (66%) of the title compound as a tan solid

Sources & evidence

ORD record
ord-38894ec5ae2640de93d8f274c33f3ff2
Source dataset
uspto-grants-2003_05
Patent number
US06559145B2

Reaction notes

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