1-Chloro-4-phenylphthalazine → HCID 178510700, compound

HRID 227794

Reaction equation

HRID 227794 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[C:12]([C:13]3[C:14]([C:18]#[N:19])=[N:15][NH:16][CH:17]=3)=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:4][CH:3]=1.Cl[C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:25][N:24]=1>CC(O)(C)C>[C:33]1([C:26]2[C:27]3[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:23]([NH:1][C:2]3[CH:21]=[CH:20][C:5]([O:6][C:7]4[C:12]([C:13]5[C:14]([C:18]#[N:19])=[N:15][NH:16][CH:17]=5)=[CH:11][CH:10]=[CH:9][N:8]=4)=[CH:4][CH:3]=3)=[N:24][N:25]=2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

4

Reactant 2

HCID 2721091-Chloro-4-phenylphthalazineHCID 178510701HCID 178510701, compound

Product 1

HCID 178510700HCID 178510700, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

In a 20-mL sealed tube was dissolved 4-(2-(4-aminophenoxy)pyridin-3-yl)-1-H-pyrazole-3-carbonitrile (0.120 g, 0.433 mmol) in t-BuOH (1.0 mL). Then 1-chloro-4-phenylphthalazine (0.104 g, 0.433 mmol) was added and the mixture was stirred at 100° C. for 3 days. The reaction was cooled to RT, concentrated and purified on a Gilson reverse phase chromatography system. The title compound was extracted into CH2Cl2, washed 1× saturated NaHCO3, 1×H2O, dried over Na2SO4, filtered through fritted funnel and concentrated. The title compound was further purified by silica gel chromatography using 10-100% EtOAc/Hexanes to afford 4-(2-(4-(4-phenylphthalazin-1-ylamino)phenoxy)pyridin-3-yl)-1-H-pyrazole-3-carbonitrile as light yellow solid. MS m/z=482 [M+1]+. Calc'd for C29H19N7O: 481.51.

Workup

  1. customIn a 20-mL sealed tube
  2. temperatureThe reaction was cooled to RT
  3. concentrationconcentrated
  4. custompurified on a Gilson reverse phase chromatography system
  5. extractionThe title compound was extracted into CH2Cl2
  6. washwashed 1× saturated NaHCO3, 1×H2O
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered through fritted funnel
  9. concentrationconcentrated
  10. customThe title compound was further purified by silica gel chromatography

Sources & evidence

ORD record
ord-018b3083fead45809ce847d29c48e976
Source dataset
uspto-grants-2009_07
Patent number
US07560551B2

Linked notes

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