Ammonium trifluoroacetate → HCID 178487663, compound

HRID 332862Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3[CH:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:10]=3[C:9]=2[O:19][C:20]2[CH:33]=[CH:32][C:23](/[CH:24]=[CH:25]/[C:26]3O[C:28]([CH3:31])=[N:29][N:30]=3)=[CH:22][CH:21]=2)=[C:4]([CH3:34])[CH:3]=1.FC(F)(F)C([O-])=O.[NH4+:42]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3[CH:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:10]=3[C:9]=2[O:19][C:20]2[CH:33]=[CH:32][C:23](/[CH:24]=[CH:25]/[C:26]3[NH:42][C:28]([CH3:31])=[N:29][N:30]=3)=[CH:22][CH:21]=2)=[C:4]([CH3:34])[CH:3]=1

Participants

Conditions

Temperature: 180 °C

Procedure

To a microwave vial, (E)-2-(4-((2-(4-fluoro-2-methylphenyl)-6-methoxybenzo[b]thiophen-3-yl)oxy)styryl)-5-methyl-1,3,4-oxadiazole (23 mg, 0.049 mmol) and ammonium trifluoroacetate (128 mg, 0.973 mmol) were suspended in toluene (2 mL). The reaction was heated for 18 h at 180° C. under microwave irradiation. The reaction mixture was concentrated and the crude product was purified by reverse phase HPLC (neutral condition, 0.1% TFA in 20-100% CH3CN/H2O) to afford (E)-3-(4-((2-(4-fluoro-2-methylphenyl)-6-methoxybenzo[b]thiophen-3-yl)oxy)styryl)-5-methyl-4H-1,2,4-triazole (15 mg, 0.032 mmol, 65% yield) as a white solid. LC/MS (m/z, MH+): 472.1.

Workup

concentrationThe reaction mixture was concentrated
customthe crude product was purified by reverse phase HPLC (neutral condition, 0.1% TFA in 20-100% CH3CN/H2O)

Sources & evidence

ORD record: ord-dd69b75c3587447eb33bc9a920ba4625
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877801B2

Reaction notes

Loading…