4-Chlorobenzylamine → N-(4-Chlorobenzyl)-6-(4-morpholinylmethyl)-4-oxo-1-phenyl-1,4-dihydrothieno[2,3-c]pyridazine-3-carboxamide

HRID 411247Notes

Reaction equation

HRID 411247 reaction equation
[N:1]1([CH2:7][C:8]2[S:27][C:11]3[N:12]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[N:13]=[C:14]([C:17]([O:19]C)=O)[C:15](=[O:16])[C:10]=3[CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH2:34])=[CH:31][CH:30]=1>>[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH:34][C:17]([C:14]2[C:15](=[O:16])[C:10]3[CH:9]=[C:8]([CH2:7][N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)[S:27][C:11]=3[N:12]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:13]=2)=[O:19])=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 660364-ChlorobenzylamineHCID 22397202Methyl 6-(4-morpholinylmethyl)-4-oxo-1-phenyl-1,4-dihydrothieno[2,3-c]pyridazine-3-carboxylate

Product 1

HCID 22397250N-(4-Chlorobenzyl)-6-(4-morpholinylmethyl)-4-oxo-1-phenyl-1,4-dihydrothieno[2,3-c]pyridazine-3-carboxamideYield 65%

Procedure

A solution of methyl 6-(4-morpholinylmethyl)-4-oxo-1-phenyl-1,4-dihydrothieno[2,3-c]pyridazine-3-carboxylate (0.29 g) in 4-chlorobenzylamine (2 mL) is heated to 190 ° C. for 30 min. The reaction mixture is cooled to ambient temperature, the solvent is removed in vacuo and Et2O (15 mL) is added to the residue. The resulting precipitate is filtered and rinsed with Et2O to afford 0.24 g (65%) of the title compound as a tan solid. Physical characteristics: m.p. 182-184° C.; 1H NMR (400 MHz, CDCl3) δ 10.56, 7.71, 7.58, 7.42, 7.32, 4.69, 3.71, 3.65, 2.51; IR (diffuse reflectance) 1677, 1587, 1549, 1532, 1508, 1493, 1347, 1297, 1278, 1261, 1115, 1112, 799, 777, 701 cm−1; MS (EI) m/z 494 (M+); HRMS (FAB) m/z 495.1265 (C25H23ClN4O3S+H). Anal. Found: C, 60.18; H, 4.79; N, 11.04.

Workup

  1. customthe solvent is removed in vacuo and Et2O (15 mL)
  2. additionis added to the residue
  3. filtrationThe resulting precipitate is filtered
  4. washrinsed with Et2O

Sources & evidence

ORD record
ord-4d8de18ad73e4dd0b995a42ee1e23193
Source dataset
uspto-grants-2003_05
Patent number
US06559145B2

Reaction notes

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