Trifluoroacetic acid → HCID 50914132, compound

HRID 1187439Notes

Reaction equation

HRID 1187439 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:20]2[CH:29]=[CH:28][C:23]([C:24]([NH:26][NH2:27])=[O:25])=[CH:22][CH:21]=2)=[CH:4][CH:3]=1.[C:30](O)(C(F)(F)F)=O>C(OC(OCC)OCC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[N:11][C:10]=2[C:20]2[CH:21]=[CH:22][C:23]([C:24]([NH:26][NH2:27])=[O:25])=[CH:28][CH:29]=2)=[CH:4][CH:3]=1.[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[N:11][C:10]=2[C:20]2[CH:21]=[CH:22][C:23]([C:24]3[O:25][CH:30]=[N:27][N:26]=3)=[CH:28][CH:29]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58119388HCID 58119388, compound

Product 2

HCID 50914132HCID 50914132, compoundHCID 58119388HCID 58119388, compound

Reagents, catalysts & solvents 1

HCID 31214Ethyl orthoformateSolvent

Conditions

Temperature
130 °C

Procedure

4-{5-[(4-chlorophenyl)thio]-2-phenyl-1,3-oxazol-4-yl}benzohydrazide from Step C (33 mg, 0.077 mmol) was dissolved in 5 mL triethylorthoformate. A catalytic amount of TFA was added and the reaction was heated at 130° C. for 2 h. The volatiles were removed and the residue was purified by reverse phase HPLC to afford 12 mg (36% over 4 steps) of the title compound 2-(4-{5-[(4-chlorophenyl)thio]-2-phenyl-1,3oxazol-4-yl}phenyl)-1,3,4-oxadiazole. LCMS: m/z 432.1 (M+H)+. 1H NMR (500 MHz, CDCl3: δ 8.55 (1H, s), 8.40 (2H, d), 8.19 (4H, br), 7.55 (3H, br), 7.30 (4H, br).

Workup

  1. customThe volatiles were removed
  2. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-3b236501fd0c45d0b1ad48624bc07496
Source dataset
uspto-grants-2014_03
Patent number
US08673941B2

Reaction notes

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