Ammonia → HCID 178489931, compound

HRID 1663004Notes

Reaction equation

HRID 1663004 reaction equation
[CH:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([NH2:10])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[CH:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[N:13][N:12]=1.C[CH2:22][O:23][C:24]([CH3:26])=O.[NH3:27]>O>[CH:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([CH2:4][C:1]3[CH:2]=[N:27][C:24]([O:23][CH3:22])=[CH:26][CH:3]=3)=[N:13][N:12]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 9207PhthalazineHCID 178448118HCID 178448118, compound

Product 1

HCID 178489931HCID 178489931, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under N2 atmosphere, in an ampoule 1.8 g (12.7 mMol) of trans 4-isopropyl-cyclohexylamine (preparation see Arzneim. Forsch. 1969, 19, 140) and 700 mg (2.4 mMol) of 1-chloro-4-[6-methoxy-pyridin-3-yl)methyl]phthalazine are heated during 14 h at 140° C. The suspension is dissolved by dilution with EtOAc, 1.5 ml of NH3 solution (25%) and water, and the aqueous phase is removed and extracted twice with EtOAc. The organic phases are washed with water and brine, dried (Na2SO4) and evaporated. Crystallization from EtOAc/hexane 1:1 results in the title compound: M.p. 124-125° C.; FAB-MS: (M+H)+=391; HPLC(Grad20-100) tRet12.4.

Workup

  1. customthe aqueous phase is removed
  2. extractionextracted twice with EtOAc
  3. washThe organic phases are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customCrystallization from EtOAc/hexane 1:1

Sources & evidence

ORD record
ord-4ceb48b07d4646b3bb1e98cfb54e0d38
Source dataset
uspto-grants-2011_10
Patent number
US08034814B2

Reaction notes

Loading…