Hydrochloric Acid → HCID 19913669, compound

HRID 1090716Notes

Reaction equation

HRID 1090716 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[N:7][N:8]3[C:15](=[O:16])[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:13][C:12]([C:23]([N:25]4[CH2:28][CH:27]([O:29][CH3:30])[CH2:26]4)=[O:24])=[C:9]32)=[CH:4][CH:3]=1.C([BH3-])#N.[Na+].Cl>CO>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][NH:7][N:8]3[C:15](=[O:16])[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:13][C:12]([C:23]([N:25]4[CH2:26][CH:27]([O:29][CH3:30])[CH2:28]4)=[O:24])=[C:9]32)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3066687Azetidine, 1-((10-chloro-4-oxo-3-phenyl-4H-pyrido(2,1-a)phthalazin-1-yl)carbonyl)-3-methoxy-HCID 5003444Sodium cyanoborohydride

Product 1

HCID 19913669HCID 19913669, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.26 g of 1-[(10-chloro-4-oxo-3-phenyl-4H-pyrido[2,1-a]phthalazin-1-yl)carbonyl]-3-methoxyazetidine and 0.75 g of sodium cyanoborohydride in 30 ml of methanol are treated dropwise at room temperature under argon with saturated methanolic hydrochloric acid. The reaction is completed after a short time. The mixture is poured into 70 ml of ice-water and the yellowish crystals are removed by filtration. The crystals are washed three times with 2 ml of water each time and dried at 60° in vacuo. After recrystallization of the crude product from ethyl acetate/acetone (1:1), there is obtained 1-[(10-chloro-6,7-dihydro-4-oxo-3-phenyl-4H-pyrido[2,1-a]phthalazin-1-yl)carbonyl]-3-methoxyazetidine as yellowish crystals of m.p. 238°-239°.

Workup

  1. customthe yellowish crystals are removed by filtration
  2. washThe crystals are washed three times with 2 ml of water each time
  3. customdried at 60° in vacuo
  4. customAfter recrystallization of the crude product from ethyl acetate/acetone (1:1)

Sources & evidence

ORD record
ord-9878248746614386a15048b0652a7440
Source dataset
uspto-grants-1992_01
Patent number
US05082842

Reaction notes

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