Trifluoroacetic acid → HCID 121254619, compound

HRID 530435Notes

Reaction equation

HRID 530435 reaction equation
[NH2:1][C:2]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]1[C:13]1[S:17][CH:16]=[C:15]([NH:18]C(=O)OC(C)(C)C)[CH:14]=1)=[O:3].FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:18][C:15]1[CH:14]=[C:13]([C:5]2[N:4]([C:2]([NH2:1])=[O:3])[C:12]3[C:7]([CH:6]=2)=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:17][CH:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 121261625HCID 121261625, compound

Product 1

HCID 121254619HCID 121254619, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To the mixture of tert-butyl {5-[1-(aminocarbonyl)-1H-indol-2-yl]-3-thienyl}carbamate (20 mg, 0.056 mmol, 1 eq) in anhydrous DCM (1 mL) at 0° C. was added dropwise trifluoroacetic acid (0.2 mL) and the resulting reaction solution was stirred at 0° C. for 45 minutes. An additional trifluoroacetic acid (0.2 mL) was added followed by a stirring at room temperature for 15 minutes. The solution was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate. The organic layer was isolated, washed once with brine, and dried with anhydrous sodium sulfate. The Upper solution was decanted, concentrated, and the brown oily residue was subject to a column chromatography (EtOAc-Hex 1:10 to 3:1) to yield 2-(4-amino-2-thienyl)-1H-indole-1-carboxamide as a yellow oil in amount of 11 mg.

Workup

  1. customthe resulting reaction solution
  2. customstirring at room temperature
  3. customfor 15 minutes
  4. customThe solution was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate
  5. customThe organic layer was isolated
  6. washwashed once with brine
  7. dry with materialdried with anhydrous sodium sulfate
  8. customThe Upper solution was decanted
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-13174d8ddd3f4e689cfec5ec1471ad99
Source dataset
uspto-grants-2016_05
Patent number
US09353093B2

Reaction notes

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