4-Chlorobenzylamine → N-(4-Chlorobenzyl)-3,7-dimethyl-2-(morpholin-4-ylmethyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide

HRID 2307307Notes

Reaction equation

[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[C:8]([C:12](OCC)=[O:13])=[CH:7][N:6]([CH3:17])[C:5]=2[S:4][C:3]=1[CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.[Cl:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][NH2:31])=[CH:28][CH:27]=1>CO>[Cl:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][NH:31][C:12]([C:8]2[C:9](=[O:11])[C:10]3[C:2]([CH3:1])=[C:3]([CH2:18][N:19]4[CH2:20][CH2:21][O:22][CH2:23][CH2:24]4)[S:4][C:5]=3[N:6]([CH3:17])[CH:7]=2)=[O:13])=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 190 °C

Procedure

A mixture of ethyl 3,7-dimethyl-2-(morpholin-4-ylmethyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylate (Preparation 28, 700 mg) and 4-chloro-benzylamine (1.25 mL) is heated to 190° C. under a nitrogen atmosphere for 1 h. The reaction mixture is allowed to cool briefly and methanol (10 mL) is added. After cooling to room temperature, the product is filtered and washed with methanol and diethyl ether to afford 634 mg of the title compound as a white solid. Physical characteristics. M.p. 222-224° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.67, 8.66, 7.41-7.33, 4.52, 3.92, 3.67, 3.59, 2.51, 2.47; MS (ESI+) m/z 446 (M+H)+. Anal. Found: C, 59.11; H, 5.47; N, 9.32; Cl, 7.96; S, 7.17.

Workup

temperatureto cool briefly
temperatureAfter cooling to room temperature
filtrationthe product is filtered
washwashed with methanol and diethyl ether

Sources & evidence

ORD record: ord-81f56b9743984273b5332a45bfabe381
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06831081B2

Reaction notes

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