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 1688901Notes

Reaction equation

HRID 1688901 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-36c391aa1c3a4309910d5152d5f16642
Source dataset
uspto-grants-2012_04
Patent number
US08148383B2

Reaction notes

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