Sodium cyanoborohydride → HCID 19913707, compound

HRID 1090719Notes

Reaction equation

HRID 1090719 reaction equation
[O:1]=[C:2]1[N:7]2[N:8]=[CH:9][C:10]3[CH:14]=[CH:13][S:12][C:11]=3[C:6]2=[C:5]([C:15]([O:17][CH3:18])=[O:16])[CH:4]=[C:3]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:25]([BH3-])#N.[Na+]>C(O)=O.O1CCCC1>[CH3:25][N:8]1[CH2:9][C:10]2[CH:14]=[CH:13][S:12][C:11]=2[C:6]2=[C:5]([C:15]([O:17][CH3:18])=[O:16])[CH:4]=[C:3]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:2](=[O:1])[N:7]12

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 15640828HCID 15640828, compound

Product 1

HCID 19913707HCID 19913707, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.34 g of methyl 7-oxo-8-phenyl-7H-pyrido[1,2-b]thieno[2,3-d]pyridazine-10-carboxylate in 10 ml of formic acid are treated dropwise under argon at 25°-30° with 0.31 g of sodium cyanoborohydride in 2 ml of tetrahydrofuran. The mixture is left to stir at room temperature for 24 hours. The solution is poured into 50 ml of ice-water. The yellowish crystals are removed by filtration and washed with water. After drying in vacuo, recrystallization is carried out from ethyl acetate. There is obtained methyl 4,5-dihydro-5-methyl-7-oxo-8-phenyl-7H-pyrido[1,2-b]thieno[2,3-d]-pyridazine-10-carboxylate of m.p. 180°-181°.

Workup

  1. waitThe mixture is left
  2. customThe yellowish crystals are removed by filtration
  3. washwashed with water
  4. customAfter drying in vacuo, recrystallization

Sources & evidence

ORD record
ord-32a705bef19547558a524fc518339416
Source dataset
uspto-grants-1992_01
Patent number
US05082842

Reaction notes

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