Phthalazine → HCID 178441005, compound

HRID 747853Notes

Reaction equation

HRID 747853 reaction equation
[C:1]([C:5]1[CH:30]=[CH:29][C:8]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH2:20][C:21]3[CH:22]=[N:23][C:24]([O:27]C)=[CH:25][CH:26]=3)=[N:12][N:11]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(C1C=CC(N)=CC=1)(C)(C)C.Cl.O1CCOCC1.C1C2C(=CC=CC=2)C=NN=1>CO.CCOC(C)=O.O.N>[C:1]([C:5]1[CH:30]=[CH:29][C:8]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH2:20][C:21]3[CH:22]=[N:23][C:24]([OH:27])=[CH:25][CH:26]=3)=[N:12][N:11]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

9

Reactant 4

HCID 9207PhthalazineHCID 698614-Tert-ButylanilineHCID 10200902HCID 10200902, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 178441005HCID 178441005, compound

Reagents, catalysts & solvents 4

HCID 222AmmoniaSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

1-(4-tert-Butyl-anilino)-4-[6-methoxy-(pyridin-3-yl)-methyl]-phthalazine: 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 ftile 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 ftile compound crystallizes out

Sources & evidence

ORD record
ord-162bb0c2ca0d46429d5b27bc7aab2761
Source dataset
uspto-grants-2008_07
Patent number
US07399761B2

Reaction notes

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