Trifluoroacetic acid → HCID 58042321, compound

HRID 1619653Notes

Reaction equation

HRID 1619653 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:47]=[C:46]([S:48]([N:51](CC2C=CC(OC)=CC=2OC)[C:52]2[S:53][CH:54]=[N:55][N:56]=2)(=[O:50])=[O:49])[C:45]([F:68])=[CH:44][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)=[CH:14][C:13]=1[C:28]1[N:32]([CH:33]2[CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34]2)[N:31]=[CH:30][CH:29]=1>ClCCl>[NH:35]1[CH2:34][CH:33]([N:32]2[C:28]([C:13]3[CH:14]=[C:15]([C:18]4[CH:19]=[CH:20][C:21]([C:24]([F:26])([F:27])[F:25])=[CH:22][CH:23]=4)[CH:16]=[CH:17][C:12]=3[O:11][C:10]3[C:9]([Cl:8])=[CH:47][C:46]([S:48]([NH:51][C:52]4[S:53][CH:54]=[N:55][N:56]=4)(=[O:50])=[O:49])=[C:45]([F:68])[CH:44]=3)=[CH:29][CH:30]=[N:31]2)[CH2:36]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58042295HCID 58042295, compound

Product 1

HCID 58042321HCID 58042321, compoundYield 127.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

Trifluoroacetic acid (0.50 mL, 6.53 mmol) was added to a solution of tert-butyl 3-{5-[4-(2-chloro-4-{[(2,4-dimethoxybenzyl)(1,3,4-thiadiazol-2-yl)amino]sulfonyl}-5-fluorophenoxy)-4′-(trifluoromethyl)biphenyl-3-yl]-1H-pyrazol-1-yl}azetidine-1-carboxylate (Preparation 40, 419 mg, 0.465 mmol) in dichloromethane (20 mL). The mixture was then heated to 40° C. for 18 hours under an atmosphere of nitrogen. The reaction was then cooled to room temperature and concentrated in vacuo to afford a brown residue (385.4 mg). The residue was purified by preparative HPLC (Trilution method) to afford the title compound as a white solid (46.3 mg, 11% over 2 steps).

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d6596ca620cd42e3a4d9520ee1e02741
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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