Water → HCID 178448116, compound

HRID 1662997Notes

Reaction equation

HRID 1662997 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:27]=[CH:26][N:25]=[C:24]([O:28]C)[CH:23]=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:27]=[CH:26][N:25]=[C:24]([OH:28])[CH:23]=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 178489122HCID 178489122, compound

Product 1

HCID 178448116HCID 178448116, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

Under N2-atmosphere, 0.28 ml (2.05 mMol) Me3Sil are added to 400 mg (1.02 mMol) of trans 1-(4-isopropyl-cyclohexylamino)-4-[2-methoxy-(pyridin-4-yl)-methyl]-phthalazine in 10 ml chloroform, and the resulting mixture is stirred during 20 h at 60° C. After cooling to RT, 5 ml sat. NaHCO3-solution, 5 ml water, 20 ml EtOAc and a small amount of methanol are added, followed by agitation. The resulting white crystals are filtered off, washed with water and dried, yielding the title compound: M.p. 266-267° C. (decomposition); FAB-MS: (M+H)+=377; HPLC(Grad20-100) tRet=10.3). From the filtrate, by extraction with EtOAc, washing of the organic phase with water and brine, drying (Na2SO4), evaporation and crystallisation from dichlormethane/methanol under addition of ether, more product results.

Workup

  1. temperatureAfter cooling to RT
  2. filtrationThe resulting white crystals are filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-27dd13208ff34f13b69d588aaea49572
Source dataset
uspto-grants-2011_10
Patent number
US08034814B2

Reaction notes

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