Phthalazine → HCID 10114725, compound

HRID 1663000Notes

Reaction equation

HRID 1663000 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH2:9][CH3:10])[NH2:5].Cl.O1[CH2:17][CH2:16][O:15][CH2:14]C1.[CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[N:20][N:19]=1>CO.CCOC(C)=O.N>[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH2:9][CH3:10])[NH:5][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([CH2:8][C:2]2[CH:3]=[CH:4][N:5]=[C:16]([O:15][CH3:14])[CH:17]=2)=[N:20][N:19]=1

Participants

7

Reactant 3

HCID 9207PhthalazineHCID 204431481,4-Dioxane hydrochlorideHCID 223456173-Bromo-4-ethylaniline

Product 1

HCID 10114725HCID 10114725, compound

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

Under N2-atmosphere, 0.73 g (3.7 mMol) 3-bromo-4-ethyl-aniline and 0.82 ml 4 N HCl/dioxane are added to 1.00 g (3.5 mMol) 1-chloro-4-[2-methoxy-pyridin-4-yl)methyl]phthalazine in 12 ml methanol, and the mixture is stirred for 2 h at 70° C. After cooling, the resulting yellow solution is diluted with EtOAc and 2.5% NH3 solution, and the aqueous phase is removed and extracted twice with EtOAct. The organic phases are washed with water and brine, dried (Na2SO4) and evaporated with a RE. After addition of DIPE to the residue, the title compound crystallizes out: M.p. 133-135° C.; FAB-MS: (M+H)+=449/451; HPLC(Grad20-100) tRet=11.4.

Workup

  1. temperatureAfter cooling
  2. customthe aqueous phase is removed
  3. extractionextracted twice with EtOAct
  4. washThe organic phases are washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated with a RE
  7. additionAfter addition of DIPE to the residue
  8. customthe title compound crystallizes out

Sources & evidence

ORD record
ord-da7711da6bec43b4af875cb40c355db2
Source dataset
uspto-grants-2011_10
Patent number
US08034814B2

Reaction notes

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