Trifluoroacetic acid → HCID 178503627, compound

HRID 589989Notes

Reaction equation

HRID 589989 reaction equation
[CH3:1][S:2][C:3]1[S:4][C:5]([C:20]2[CH:24]=[CH:23][NH:22][N:21]=2)=[C:6]2[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[C:8](=[O:19])[C:7]=12.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][S:2][C:3]1[S:4][C:5]([C:20]2[CH:24]=[CH:23][NH:22][N:21]=2)=[C:6]2[CH2:11][CH2:10][NH:9][C:8](=[O:19])[C:7]=12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178503629HCID 178503629, compound

Product 1

HCID 178503627HCID 178503627, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl 3-(methylsulfanyl)-4-oxo-1-(1H-pyrazol-3-yl)-6,7-dihydrothieno[3,4-c]pyridine-5(4H)-carboxylate (20 mg, 0.055 mmol) in CH2Cl2 (274 μL) at 0° C. was added TFA (274 μL). The solution was stirred at 0° C. for 15 min. The resulting mixture was quenched with saturated aq. NaHCO3 and extracted with CH2Cl2. The combined extracts were dried (Na2SO4) and concentrated. Purification by silica gel chromatography (gradient elution, 0-10% MeOH/dichloromethane) afforded the title compound. 1H NMR (400 MHz, ppm, CDCl3) δ 11.66 (s, 1 H); 8.05 (s, 1 H); 7.77 (d, J=2.6 Hz, 1 H); 6.53 (d, J=2.6 Hz, 1 H); 3.58 (t, J=6.5 Hz, 2 H); 3.07 (t, J=6.5 Hz, 2 H); 2.64 (s, 3 H). HRMS (ES+) m/z 266.0414 [(M+H)+; calcd for C11H11N3OS2: 266.0416].

Workup

  1. customThe resulting mixture was quenched with saturated aq. NaHCO3
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification
  6. washby silica gel chromatography (gradient elution, 0-10% MeOH/dichloromethane)

Sources & evidence

ORD record
ord-1d6204dba3f142f9ac48910c5a38872e
Source dataset
uspto-grants-2016_01
Patent number
US09233977B2

Reaction notes

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