Sodium hydride → Methyl 6-(4-morpholinylmethyl)-4-oxo-1-phenyl-1,4-dihydrothieno[2,3-c]pyridazine-3-carboxylate

HRID 411246Notes

Reaction equation

HRID 411246 reaction equation
Cl[C:2]1[S:3][C:4]([CH2:22][N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[CH:5][C:6]=1[C:7](=[O:21])/[C:8](=[N:13]/[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)/[C:9]([O:11][CH3:12])=[O:10].[H-].[Na+]>C1COCC1>[N:23]1([CH2:22][C:4]2[S:3][C:2]3[N:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[N:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[C:7](=[O:21])[C:6]=3[CH:5]=2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 178501725HCID 178501725, compound

Product 1

HCID 22397202Methyl 6-(4-morpholinylmethyl)-4-oxo-1-phenyl-1,4-dihydrothieno[2,3-c]pyridazine-3-carboxylateYield 16%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (2Z)-3-(2-chloro-5-(4-morpholinylmethyl)-3-thienyl)-3-oxo-2-(phenylhydrazono)propanoate (Preparation 65, 2.67 g) in dry THF (150 mL) is added NaH (0.43 g; 60% dispersion in mineral oil) portionwise at ambient temperature. The reaction is continued overnight and the solvent is removed in vacuo. Water (50 mL) is added to residue and the aqueous layer is extracted with EtOAc (3×50 mL). The organic layer is separated, dried over MgSO4, filtered, and concentrated in vacuo. The resulting precipitate is filtered to afford 0.38 g (16%) of the title compound as a brown solid. Physical characteristics: m.p. 167-169° C.; 1H NMR (400 MHz, CDCl3)δ 7.67, 7.57, 7.43, 3.98, 3.68, 2.50; IR (diffuse reflectance) 2816, 1731, 1615, 1515, 1353, 1279, 1200, 1172, 1133, 1121, 1106, 1026, 867, 809, 749 cm−1; MS (ESI+) 386; HRMS (FAB) m/z 386.1180 (C19H19N3O4S+H). Anal. Found: C, 59.14; H, 5.02; N, 10.48.

Workup

  1. customthe solvent is removed in vacuo
  2. additionWater (50 mL) is added to residue
  3. extractionthe aqueous layer is extracted with EtOAc (3×50 mL)
  4. customThe organic layer is separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. filtrationThe resulting precipitate is filtered

Sources & evidence

ORD record
ord-be7b8b9bbed94271bb918d1e073ce093
Source dataset
uspto-grants-2003_05
Patent number
US06559145B2

Reaction notes

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