Trifluoroacetic acid → HCID 86677178, compound

HRID 929353Notes

Reaction equation

HRID 929353 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([C:14]1[C:15]([F:30])=[C:16]([NH:22]C(=O)OC(C)(C)C)[CH:17]=[C:18]([F:21])[C:19]=1[F:20])=[O:13])=[CH:7][CH:6]=2.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:22][C:16]1[C:15]([F:30])=[C:14]([C:12]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[N:4]=[CH:3][C:2]([Cl:1])=[N:11]3)=[O:13])[C:19]([F:20])=[C:18]([F:21])[CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86677179HCID 86677179, compound

Product 1

HCID 86677178HCID 86677178, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (3-(3-chloroquinoxaline-6-carbonyl)-2,4,5-trifluorophenyl)carbamate (128 mg, 0.29 mmol, 1.0 eq.) in DCM (5 mL) was added TFA (5 mL). After the resulting mixture was stirred at rt for 0.5 h, the solvent was evaporated. The resulting residue was washed with saturated NaHCO3 and extracted with EA (20 mL×3). The combined organic layers were dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash column chromatography (PE/EA=2/1, v/v) to afford (3-amino-2,5,6-trifluorophenyl)(3-chloroquinoxalin-6-yl)methanone (40 mg, 40.9%).

Workup

  1. customthe solvent was evaporated
  2. washThe resulting residue was washed with saturated NaHCO3
  3. extractionextracted with EA (20 mL×3)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by flash column chromatography (PE/EA=2/1

Sources & evidence

ORD record
ord-805eef3a2c2e485cb3094bcf2339c835
Source dataset
uspto-grants-2016_03
Patent number
US09295671B2

Reaction notes

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