Ammonia → HCID 178489122, compound

HRID 1662998Notes

Reaction equation

HRID 1662998 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.[NH3:21].O.C[CH2:24][O:25][C:26]([CH3:28])=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]([CH2:5][C:4]3[CH:1]=[CH:2][N:21]=[C:26]([O:25][CH3:24])[CH:28]=3)=[N:13][N:12]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

6

Reactant 5

HCID 222AmmoniaHCID 962WaterHCID 8857Ethyl AcetateHCID 9207PhthalazineHCID 178448118HCID 178448118, compound

Product 1

HCID 178489122HCID 178489122, compound

Procedure

Under N2 atmosphere, in an ampoule 1.73 g (12 mMol) of trans 4-isopropyl-cyclohexylamine (preparation see Arzneim. Forsch. 1969, 19, 140) and 700 mg (2.4 mMol) of 1-chloro-4-[2-methoxy-pyridin-4-yl)methyl]phthalazine are heated during 17 h at 140° C. The reaction mixture is suspended in EtOAc, and 1.5 ml of NH3 solution (25%) and water are added. The isolated aqueous phase is extracted another two times with EtOAc, and the organic phases are washed with water and brine, dried (Na2SO4) and evaporated to dryness. Column chromatography (SiO2; hexane/EtOAc 1:1) results in the title compound: M.p. 65-66° C.; FAB-MS: (M+H)+=391.

Workup

  1. extractionThe isolated aqueous phase is extracted another two times with EtOAc
  2. washthe organic phases are washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-5425380acb1a4232854225d6491ca12b
Source dataset
uspto-grants-2011_10
Patent number
US08034814B2

Reaction notes

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