Hydrochloric Acid → 6-[2-(4-aminomethyl-phenyl)-benzoxazol-6-yl]-5-methyl-4,5-dihydro-2H-pyridazin-3-one

HRID 1619982Notes

Reaction equation

HRID 1619982 reaction equation
[CH3:1][CH:2]1[CH2:7][C:6](=[O:8])[NH:5][N:4]=[C:3]1[C:9]1[CH:25]=[CH:24][C:12]2[N:13]=[C:14]([C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)[O:15][C:11]=2[CH:10]=1.[H][H].Cl>[Ni].N>[NH2:21][CH2:20][C:19]1[CH:22]=[CH:23][C:16]([C:14]2[O:15][C:11]3[CH:10]=[C:9]([C:3]4[CH:2]([CH3:1])[CH2:7][C:6](=[O:8])[NH:5][N:4]=4)[CH:25]=[CH:24][C:12]=3[N:13]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 674610074-[6-(4-Methyl-6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-benzoxazol-2-yl]-benzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 674625176-[2-(4-aminomethyl-phenyl)-benzoxazol-6-yl]-5-methyl-4,5-dihydro-2H-pyridazin-3-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

100 mg (303 μmol) 4-[6-(4-methyl-6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-benzoxazol-2-yl]-benzonitrile, 10 mg Raney nickel and 20 ml of methanolic ammonia are hydrogenated at RT and 3.45 bar hydrogen pressure for 4 h. Then the mixture is neutralised with conc. hydrochloric acid and the solv. is eliminated from the reaction mixture by rotary evaporation in vacuo. The residue is purified by RP-HPLC.

Workup

  1. customare hydrogenated at RT
  2. customis eliminated from the reaction mixture by rotary evaporation in vacuo
  3. customThe residue is purified by RP-HPLC

Sources & evidence

ORD record
ord-a5243a2f870a41a78727d44bdb1c8d35
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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