Ammonia → HCID 178448116, compound

HRID 747852Notes

Reaction equation

HRID 747852 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[N:3][N:2]=1.[CH:11]([C@H:14]1[CH2:19][CH2:18][C@H:17]([NH2:20])[CH2:16][CH2:15]1)([CH3:13])[CH3:12].[NH3:21].[OH2:22]>CCOC(C)=O>[CH:11]([C@H:14]1[CH2:19][CH2:18][C@H:17]([NH:20][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]([CH2:4][C:5]3[CH:10]=[CH:9][N:21]=[C:7]([OH:22])[CH:6]=3)=[N:3][N:2]=2)[CH2:16][CH2:15]1)([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 9207Phthalazine2×HCID 178448118HCID 178448118, compound

Product 1

HCID 178448116HCID 178448116, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

trans 1-(4-isoproryl-cyclohexylamino)-4-[2-methoxy-pyridin-4-yl)-methyl]-phthalazine: 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-c6f6954f88d54203b5aac40efa587971
Source dataset
uspto-grants-2008_07
Patent number
US07399761B2

Reaction notes

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