Triphenylphosphine → 1-methyl-6-(4-(1-(pyridin-2-yl)piperidin-4-yloxy)-3-(trifluoro-methyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile

HRID 517949Notes

Reaction equation

HRID 517949 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]#[N:15])[C:11]3[N:16]=[N:17][N:18]([CH3:19])[C:10]=3[CH:9]=2)=[CH:4][C:3]=1[C:20]([F:23])([F:22])[F:21].[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N:30]1[CH2:35][CH2:34][CH:33](O)[CH2:32][CH2:31]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>CN1C(=O)CCC1>[CH3:19][N:18]1[C:10]2[CH:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([O:1][CH:33]4[CH2:32][CH2:31][N:30]([C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=5)[CH2:35][CH2:34]4)=[C:3]([C:20]([F:23])([F:22])[F:21])[CH:4]=3)[N:13]=[C:12]([C:14]#[N:15])[C:11]=2[N:16]=[N:17]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 106074171-(Pyridin-2-yl)piperidin-4-olHCID 1363523116-(4-hydroxy-3-(trifluoromethyl)-phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile

Product 1

HCID 672940871-methyl-6-(4-(1-(pyridin-2-yl)piperidin-4-yloxy)-3-(trifluoro-methyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

6-(4-hydroxy-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile (0.940 mmol, 300 mg), 1-(pyridin-2-yl)piperidin-4-ol (1.410 mmol, 251 mg) and Triphenylphosphine (1.410 mmol, 370 mg) were suspended in NMP (1 ml) and DIAD (1.410 mmol, 0.278 ml, 285 mg) added. The mixture was stirred at room temperature overnight. The reaction mixture was passed down an SCX column to afford 1-methyl-6-(4-(1-(pyridin-2-yl)piperidin-4-yloxy)-3-(trifluoro-methyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile. (0.024 g)

Sources & evidence

ORD record
ord-66da03b0a468496c8f41a3133f25e1ba
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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