Triphenylphosphine → 3,7-Di(pyridin-4-yl)-5-[2-(quinolin-2-yl)ethyl]thieno[2,3-d]pyridazin-4(5H)-one

HRID 920899Notes

Reaction equation

HRID 920899 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:15]3[C:14](=[O:16])[NH:13][N:12]=[C:11]([C:17]4[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=4)[C:10]=3[S:9][CH:8]=2)=[CH:3][CH:2]=1.[N:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[CH2:33][CH2:34]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:34][CH2:33][C:24]4[CH:25]=[CH:26][C:27]5[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=5)[N:23]=4)[N:12]=[C:11]([C:17]4[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=4)[C:10]=3[S:9][CH:8]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 705322-QuinolineethanolHCID 5363146Diisopropyl azodicarboxylateHCID 866831153,7-di(pyridin-4-yl)thieno[2,3-d]pyridazin-4(5H)-one

Product 1

HCID 715508883,7-Di(pyridin-4-yl)-5-[2-(quinolin-2-yl)ethyl]thieno[2,3-d]pyridazin-4(5H)-oneYield 17.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,7-di(pyridin-4-yl)thieno[2,3-d]pyridazin-4(5H)-one from example 1.5 (100 mg, 0.32 mmol), 2-quinolin-2-yl-ethanol from example a1 (58 mg, 0.33 mmol) and PPh3 (256 mg, 0.98 mmol) in DCM (10 mL), DIAD (198 mg, 0.98 mmol) was added dropwise. The mixture was stirred at room temperature for 3 h, concentrated and the residue was purified by Prep-HPLC to give the title compound as white solid (26 mg, 17.6% yield).

Workup

  1. concentrationconcentrated
  2. customthe residue was purified by Prep-HPLC

Sources & evidence

ORD record
ord-bfbcbf93d4984f28bf34fd1f1c416329
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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