Trifluoroacetic acid → HCID 71493952, compound

HRID 1486986Notes

Reaction equation

HRID 1486986 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]([F:45])([F:44])[C:10]1[CH:11]=[C:12]([C:20]2[N:24]=[CH:23][N:22](/[CH:25]=[CH:26]\[C:27]([NH:29][CH2:30][CH:31]3[CH2:36][CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32]3)=[O:28])[N:21]=2)[CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1>ClCCl.CO>[F:19][C:16]([F:17])([F:18])[C:14]1[CH:13]=[C:12]([C:20]2[N:24]=[CH:23][N:22](/[CH:25]=[CH:26]\[C:27]([NH:29][CH2:30][CH:31]3[CH2:36][CH2:35][CH2:34][NH:33][CH2:32]3)=[O:28])[N:21]=2)[CH:11]=[C:10]([C:9]([F:8])([F:44])[F:45])[CH:15]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89401904HCID 89401904, compound

Product 1

HCID 71493952HCID 71493952, compoundYield 146.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent3×

Procedure

In a 25 mL single neck round-bottomed flask (Z)-tert-butyl 3-((3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acrylamido)methyl)piperidine-1-carboxylate (1) (0.1 g) was dissolved in dichloromethane (5 mL) and TFA (1.0 mL) dissolved in dichloromethane added dropwise. The progress of the reaction was followed by TLC on silica gel in 10% methanol in dichloromethane as a mobile phase in UV visualization. Reaction mixture was concentrated by rotary evaporation (40° C., 20 mmHg) to afford 0.12 g of compound. The resulting crude compound was purified by ‘SAEx’ column chromatography. Fraction collected together to obtain compound (40 mg) yield 49%.

Workup

  1. additionadded dropwise
  2. customReaction mixture
  3. concentrationwas concentrated by rotary evaporation (40° C., 20 mmHg)

Sources & evidence

ORD record
ord-e7eaf11e0f7446cdb4e291a2ceb5f305
Source dataset
uspto-grants-2016_08
Patent number
US09428490B2

Reaction notes

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