Triphenylphosphine → 2-((3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)methyl)-6-(4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

HRID 2368020Notes

Reaction equation

HRID 2368020 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[N:14]([C:16](=[O:19])[NH:17][N:18]=3)[CH:15]=2)=[CH:6][CH:5]=1.[CH:22]1([C:25]2[CH:29]=[C:28]([CH2:30]O)[N:27]([CH3:32])[N:26]=2)[CH2:24][CH2:23]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH:22]1([C:25]2[CH:29]=[C:28]([CH2:30][N:17]3[C:16](=[O:19])[N:14]4[CH:15]=[C:10]([C:7]5[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:20])[F:21])=[CH:9][CH:8]=5)[CH:11]=[CH:12][C:13]4=[N:18]3)[N:27]([CH3:32])[N:26]=2)[CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 25247625(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)methanolHCID 58044589HCID 58044589, compound

Product 1

HCID 565960312-((3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)methyl)-6-(4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-(4-(Trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (50.0 mg, 0.169 mmol), (3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)methanol (38.6 mg, 0.2535, 1.5 equiv.) and PPh3 (60.5 mg, 0.2535 mmol, 1.5 equiv.) were placed in a 50 mL round bottomed flask under a nitrogen atmosphere. To the flask were added THF (3 mL) and diethyl azodicarboxylate (40% in toluene, 110.5 mg, 0.2535 mmol, 1.5 equiv.) at room temperature. The reaction mixture was stirred at the same temperature for 4 h. The reaction mixture was directly loaded onto prep-HPLC to give 2-((3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)methyl)-6-(4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one as light yellow crystals. FTIR (ATR) 1710 cm−1 (CO).

Sources & evidence

ORD record
ord-1b22d763d4da4909b7397b7731171cd2
Source dataset
uspto-grants-2014_04
Patent number
US08703759B2

Reaction notes

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