Trifluoroacetic acid → HCID 117737276, compound

HRID 1504388Notes

Reaction equation

HRID 1504388 reaction equation
[CH2:1]([S:8][C:9]1[CH:10]=[CH:11][C:12]([NH:22][C:23]2[C:28]([O:29][CH3:30])=[CH:27][C:26]([C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([CH3:38])[CH:32]=3)=[C:25]([F:39])[CH:24]=2)=[C:13]([NH:15][CH2:16][C:17](OCC)=[O:18])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([S:8][C:9]1[CH:14]=[C:13]2[C:12](=[CH:11][CH:10]=1)[N:22]([C:23]1[C:28]([O:29][CH3:30])=[CH:27][C:26]([C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([CH3:38])[CH:32]=3)=[C:25]([F:39])[CH:24]=1)[C:17](=[O:18])[CH2:16][NH:15]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117737286HCID 117737286, compound

Product 1

HCID 117737276HCID 117737276, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a microwave vial was added, ethyl 2-((5-(benzylthio)-2-((4′-chloro-2-fluoro-5-methoxy-3′-methyl-[1,1′-biphenyl]-4-yl)amino)phenyl)amino)acetate (2.00 g, 3.54 mmol) followed by DCM (11.80 ml) and TFA (2.73 ml, 35.4 mmol). The vial was placed in the microwave for 30 min at 80° C. Solvent was removed in vaccuo and sodium bicarbate solution was added. The solution was extracted with DCM and organics dried over MgSO4, filtered and removed solvent in vaccuo. Used 6-(benzylthio)-1-(4′-chloro-2-fluoro-5-methoxy-3′-methyl-[1,1′-biphenyl]-4-yl)-3,4-dihydroquinoxalin-2(1H)-one (1.43 g, 2.76 mmol, 78% yield) without further purification. m/z (ESI) 520.2 (M+H)+.

Workup

  1. additionTo a microwave vial was added
  2. customSolvent was removed in vaccuo and sodium bicarbate solution
  3. additionwas added
  4. extractionThe solution was extracted with DCM
  5. dry with materialorganics dried over MgSO4
  6. filtrationfiltered
  7. customremoved solvent in vaccuo

Sources & evidence

ORD record
ord-1bbeb25294ee4b6d8d2c6a6e664b0b12
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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