Sodium borohydride → HCID 19081395, compound

HRID 963203Notes

Reaction equation

HRID 963203 reaction equation
[NH2:1][CH:2]1[C:7](=[N:8][C:9]2[CH:14]=[CH:13]N=CC=2)[CH:6]=[N:5][N:4]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:3]1=[O:19].[BH4-].[Na+]>CO>[NH2:1][C:2]1[C:3](=[O:19])[N:4]([C:15]([CH3:16])([CH3:17])[CH3:18])[N:5]=[CH:6][C:7]=1[NH:8][CH2:9][C:14]1[CH:13]=[CH:15][N:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 19081415HCID 19081415, compound

Product 1

HCID 19081395HCID 19081395, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into 150 ml of an absolute methanol solution of 10.8 g of 4-amino-2-tert-butyl-5-(4-pyridylimino)pyridazin-3-(2H)-one, 0.76 g of sodium borohydride was added in a few times under cooling with ice. Then, the mixture was stirred at room temperature for 40 minutes, and the 0.76 g of sodium borohydride was further added thereto. The mixture was stirred for 0.5 hour. Methanol was distilled off under reduced pressure, and 200 ml of water and 400 ml of ethyl acetate were added to the residue, followed by shaking. The insoluble powder was collected by filtration. The organic layer in the filtrate was dried over anhydrous sodium sulfate and distilled under reduced pressure to obtain 4.7 g of a residue. The residue was combined to the previously obtained insoluble powder, and the mixture was thoroughly washed with a solvent mixture comprising 150 ml of n-hexane and 50 ml of methylene chloride, and then dried to obtain 8.7 g of the desired product (Compound No. 10) having a melting point of from 219° to 225° C.

Workup

  1. temperatureunder cooling with ice
  2. stirringThe mixture was stirred for 0.5 hour
  3. distillationMethanol was distilled off under reduced pressure, and 200 ml of water and 400 ml of ethyl acetate
  4. additionwere added to the residue
  5. stirringby shaking
  6. filtrationThe insoluble powder was collected by filtration
  7. dry with materialThe organic layer in the filtrate was dried over anhydrous sodium sulfate
  8. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-ec6da82b540749cbb6607ab1e5275fe0
Source dataset
uspto-grants-1998_06
Patent number
US05763439

Reaction notes

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