Ammonia → HCID 53446128, compound

HRID 1020717Notes

Reaction equation

HRID 1020717 reaction equation
[ClH:1].[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[C:5]([N:17]([CH2:19][CH2:20][C:21]#N)[CH3:18])[N:4]=1.[NH3:23]>C(Cl)Cl.[Ni]>[ClH:1].[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[C:5]([N:17]([CH3:18])[CH2:19][CH:20]([NH2:23])[CH3:21])[N:4]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 13544732HCID 13544732, compound

Product 1

HCID 53446128HCID 53446128, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6344DichloromethaneSolvent

Procedure

25 gms, 0.77 moles of N-(4-amino-6,7-dimethoxyquinazol-2-yl)-N-methyl-2-cyanoethylamine hydrochloride, 25 gms of Raney-Nickel and 500 ml of 9.8% methanolic ammonia solution were charged in an autoclave. The reaction mixture was hydrogenated at 70° C. under a pressure of 5 kg/cm2 (70 psi) for 2 hours. The reaction mass was cooled to room temperature, filtered on hyflo bed and washed with 200 ml methanol. The solvent was distilled under reduced pressure. The residue obtained was stirred in 50 ml methylene chloride and concentrated under reduced pressure at 40° C. The residue was dissolved in 200 ml isopropanol and acidified to pH 1-2 with isopropanolic HCl. The N-(4-amino-6,7-dimethoxyquinazol-2-yl)-N-methyl propylenediamine hydrochloride obtained was isolated by filtration and dried under suction.

Workup

  1. filtrationfiltered on hyflo bed
  2. washwashed with 200 ml methanol
  3. distillationThe solvent was distilled under reduced pressure
  4. customThe residue obtained
  5. concentrationconcentrated under reduced pressure at 40° C
  6. dissolutionThe residue was dissolved in 200 ml isopropanol

Sources & evidence

ORD record
ord-bf82aa805ff84b35ac0ec55f92a4cbff
Source dataset
uspto-grants-2014_05
Patent number
US08716476B2

Reaction notes

Loading…