Sodium hydride → HCID 86743626, compound

HRID 1090722Notes

Reaction equation

HRID 1090722 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:6](=[O:16])[N:7]2[C:12]=1[C:11]1[S:13][CH:14]=[CH:15][C:10]=1[CH2:9][NH:8]2.[H-].[Na+].Cl[C:26]([N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1)=[O:27]>CN(C)C=O>[O:16]=[C:6]1[N:7]2[NH:8][CH2:9][C:10]3[CH:15]=[CH:14][S:13][C:11]=3[C:12]2=[C:3]([CH2:2][O:1][C:26]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[O:27])[CH:4]=[C:5]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 848104-Morpholinecarbonyl chlorideHCID 19913664HCID 19913664, compound

Product 1

HCID 86743626HCID 86743626, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2.62 g of 4,5-dihydro-10-(hydroxymethyl)-8-phenyl-7H-pyrido[1,2-b]thieno[2,3-d]pyridazin-7-one are dissolved in 80 ml of N,N-dimethylformamide and cooled to 3° in an ice-bath. 440 mg of 55 percent sodium hydride (NaH) dispersion are added portionwise thereto and the mixture is stirred for an additional hour after the last portion has been added. A solution of 1.5 g of N-chlorocarbonylmorpholine in 3 ml of N,N-dimethylformamide is now added dropwise thereto. The reaction mixture is left to stir at about 5° for an additional 45 minutes and poured into 800 ml of ice-water, whereby the crude product crystallizes out. After washing with water and drying, the crude product is purified by chromatography on silica gel and recrystallization. There is obtained (4,5-dihydro-7-oxo-8-phenyl-7H-pyrido[1,2-b]-thieno[2,3-d]pyridazin-10-yl)methyl-4-morpholinecarboxylate of m.p. 207°-210° (acetonitrile).

Workup

  1. temperaturecooled to 3° in an ice-bath
  2. additionhas been added
  3. waitThe reaction mixture is left
  4. stirringto stir at about 5° for an additional 45 minutes
  5. customcrystallizes out
  6. washAfter washing with water
  7. customdrying
  8. customthe crude product is purified by chromatography on silica gel and recrystallization

Sources & evidence

ORD record
ord-5af01fdf321b4d23a268e3de0a77d5ea
Source dataset
uspto-grants-1992_01
Patent number
US05082842

Reaction notes

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