Triphenylphosphine → 2-[4-Chloro-5-(3-fluorophenyl)-3-phenyl-pyrazolo[3,4-c]pyridazin-1-yl]-1-pyrrolidin-1-yl-ethanone

HRID 1615726Notes

Reaction equation

HRID 1615726 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[N:6][N:5]=[C:4]2[NH:15][N:16]=[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:3]=12.O[CH2:25][C:26]([N:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)=[O:27].N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[N:6][N:5]=[C:4]2[N:15]([CH2:25][C:26]([N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)=[O:27])[N:16]=[C:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:3]=12

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 64804852-Hydroxy-1-(pyrrolidin-1-yl)ethan-1-oneHCID 86717365CID 86717365

Product 1

HCID 737761822-[4-Chloro-5-(3-fluorophenyl)-3-phenyl-pyrazolo[3,4-c]pyridazin-1-yl]-1-pyrrolidin-1-yl-ethanone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-chloro-5-(3-fluorophenyl)-3-phenyl-1H-pyrazolo[3,4-c]pyridazine (0.33 mmol), 2-hydroxy-1-(pyrrolidin-1-yl)ethanone (0.65 mmol), diethyl azodicarboxylate (114 mg, 0.65 mmol) and triphenyl phosphine (171 mg, 0.65 mmol) in 1,4-dioxane (2 mL) was heated using microwave irradiation to a temperature between 85 and 120° C. for a 30 to 90 min period. The reaction mixture was concentrated in vacuo and the residue was purified by preparative HPLC to provide Compound 11.

Workup

  1. temperaturewas heated
  2. custommicrowave irradiation to a temperature between 85 and 120° C. for a 30 to 90 min period
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-0ffc2a98f2514604b72b6420b9a67ea0
Source dataset
uspto-grants-2014_07
Patent number
US08765762B2

Reaction notes

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