Trifluoroacetic acid → 6-{[3-fluoro-2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-one

HRID 519936Notes

Reaction equation

HRID 519936 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:11](=[O:12])[C:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[NH:30][C:29](=[O:31])[O:28][N:27]=3)=[CH:16][C:15]=2[F:32])=[C:9]([CH2:33][CH2:34][CH3:35])[N:8]2[N:36]=[CH:37][N:38]=[C:7]12.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[F:32][C:15]1[CH:16]=[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]2[NH:30][C:29](=[O:31])[O:28][N:27]=2)[CH:18]=[CH:19][C:14]=1[CH2:13][C:10]1[C:11](=[O:12])[NH:6][C:7]2[N:8]([N:36]=[CH:37][N:38]=2)[C:9]=1[CH2:33][CH2:34][CH3:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 1360637614-(2,4-dimethoxybenzyl)-6-{[3-fluoro-2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-one

Product 1

HCID 1360639186-{[3-fluoro-2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-oneYield 10%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-(2,4-dimethoxybenzyl)-6-{[3-fluoro-2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-one (0.3 g), trifluoroacetic acid (5 mL) and toluene (5 mL) was stirred at room temperature for 16 hr. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography to give the title compound as a colorless amorphous solid (0.022 g, 10%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dbc179d6ae67432b928f0b738db3534f
Source dataset
uspto-grants-2015_08
Patent number
US09115136B2

Reaction notes

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