Trifluoroacetic acid → HCID 178474075, compound

HRID 2402094Notes

Reaction equation

HRID 2402094 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[C:12]([C:38]#[N:39])=[C:13]([C:27]3[CH:32]=[CH:31][N+:30]([O-:33])=[C:29]([NH:34][C:35](=[O:37])[CH3:36])[CH:28]=3)[S:14][C:15]=2[C:16]2[N:20]=[CH:19][N:18](C3CCCCO3)[N:17]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[C:12]([C:38]#[N:39])=[C:13]([C:27]3[CH:32]=[CH:31][N+:30]([O-:33])=[C:29]([NH:34][C:35](=[O:37])[CH3:36])[CH:28]=3)[S:14][C:15]=2[C:16]2[NH:20][CH:19]=[N:18][N:17]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178474069HCID 178474069, compound

Product 1

HCID 178474075HCID 178474075, compoundYield 66.3%

Procedure

N-(4-{4-[(4-chlorophenyl)sulfonyl]-3-cyano-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-2-thienyl}-1-oxidopyridin-2-yl)acetamide (0.0742 g, 0.127 mmol) was dissolved in trifluoroacetic acid (4.00 mL, 51.9 mmol). The mixture was stirred at room temperature for 4 hrs, solvent was evaporated and the residue was purified by HPLC to yield a solid product (0.0421 g, yield 66.3%) LCMS: (AA) ES+ 501, 503. 1H NMR (300 MHz, MeOD) δ: 8.90 (s, 1H), 8.60 (s, 1H), 8.43 (d, 1H), 8.35 (d, 2H), 7.67 (d, 2H), 7.59 (d, 1H), 2.28 (s, 3H).

Workup

  1. customsolvent was evaporated
  2. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-285eeee49b904e329c6a80300fb2f236
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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