Water → HCID 178448115, compound

HRID 1663003Notes

Reaction equation

HRID 1663003 reaction equation
[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]([CH2:21][C:22]3[CH:23]=[N:24][C:25]([O:28]C)=[CH:26][CH:27]=3)=[N:13][N:12]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].O.CCOC(C)=O>C(Cl)(Cl)Cl.CO>[CH:1]([C@H:4]1[CH2:5][CH2:6][C@H:7]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([CH2:21][C:22]3[CH:23]=[N:24][C:25]([OH:28])=[CH:26][CH:27]=3)=[N:13][N:12]=2)[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 178489931HCID 178489931, compound

Product 1

HCID 178448115HCID 178448115, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

Under N2 atmosphere, 0.35 ml (2.6 mMol) of Me3Sil are added to 500 mg (1.3 mMol) of trans 1-(4-isopropyl-cyclohexylamino)-4-[6-methoxy-(pyridin-3-yl)-methyl]-phthalazine in 15 ml of chloroform, followed by stirring for 16 h at 60° C. After cooling to RT, 15 ml of sat. NaHCO3 solution, 10 ml of water, EtOAc and a small amount of methanol are added, followed by agitation. From the resulting solution, the aqueous phase is removed and extracted twice with EtOAc. The organic phases are washed with water and brine, dried (Na2SO4) and evaporated to dryness. Crystallization by partial evaporation of a solution in methanol results in the title compound: M.p. 271-272° C. (decomposition); FAB-MS: (M+H)+=377; HPLC(Grad20-100) tRet=10.2.

Workup

  1. temperatureAfter cooling to RT
  2. customFrom the resulting solution, the aqueous phase is removed
  3. extractionextracted twice with EtOAc
  4. washThe organic phases are washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated to dryness
  7. customCrystallization
  8. customby partial evaporation of a solution in methanol

Sources & evidence

ORD record
ord-6e12803540354716b8c7cc8bba4ae9e5
Source dataset
uspto-grants-2011_10
Patent number
US08034814B2

Reaction notes

Loading…