Phthalazine → HCID 10200902, compound

HRID 1663002Notes

Reaction equation

HRID 1663002 reaction equation
[C:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.O1[CH2:18][CH2:17][O:16][CH2:15]C1.[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[N:21][N:20]=1>CO.CCOC(C)=O.O.N>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([NH:9][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]([CH2:23][C:28]3[CH:19]=[N:20][C:17]([O:16][CH3:15])=[CH:18][CH:27]=3)=[N:21][N:20]=2)=[CH:10][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 3

HCID 9207PhthalazineHCID 698614-Tert-ButylanilineHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 10200902HCID 10200902, compound

Reagents, catalysts & solvents 4

HCID 222AmmoniaSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

Under N2 atmosphere, 0.40 g (2.7 mMol) of 4-tert-butyl-aniline and 0.62 ml 4 N HCl/dioxane are added to 750 mg (2.6 mMol) of 1-chloro-4-[6-methoxy-pyridin-3-yl)methyl]phthalazine in 11 ml of methanol, and the mixture is stirred for 2 h at 65° C. After cooling, the resulting yellow solution is diluted with EtOAc, 20 ml of water and 10 ml of 2.5% NH3 solution, and the aqueous phase is removed and extracted twice with EtOAc. The organic phases are washed with water and brine, dried and partially evaporated with a RE. After addition of DIPE to the remnant, the title compound crystallizes out: FAB-MS: (M+H)+=399; HPLC(Grad20-100) tRet=11.9.

Workup

  1. temperatureAfter cooling
  2. customthe aqueous phase is removed
  3. extractionextracted twice with EtOAc
  4. washThe organic phases are washed with water and brine
  5. customdried
  6. custompartially evaporated with a RE
  7. additionAfter addition of DIPE to the remnant
  8. customthe title compound crystallizes out

Sources & evidence

ORD record
ord-9b5fb6de1e9b4d76b26297dd3b71ed2c
Source dataset
uspto-grants-2011_10
Patent number
US08034814B2

Reaction notes

Loading…