HCID 86731676, compound → HCID 86731677, compound

HRID 1504785Notes

Reaction equation

HRID 1504785 reaction equation
COC1C=C(OC)C=CC=1C[NH:6][C:7]1[N:8]=[C:9]([CH3:16])[CH:10]=[C:11]2[CH:15]=[CH:14][S:13][C:12]=12>FC(F)(F)C(O)=O>[CH3:16][C:9]1[CH:10]=[C:11]2[CH:15]=[CH:14][S:13][C:12]2=[C:7]([NH2:6])[N:8]=1

Participants

3

Reactant 1

HCID 86731676HCID 86731676, compound

Product 1

HCID 86731677HCID 86731677, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N-(2,4-dimethoxybenzyl)-5-methylthieno[2,3-c]pyridin-7-amine (235 mg, 0.747 mmol) in trifluoroacetic acid (6 mL) was heated to 40° C. for 1 hour. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Toluene was added to the flask and the reaction mixture was concentrated under reduced pressure again. The residue was diluted with 10% 2-propanol/chloroform (30 mL), saturated aqueous sodium bicarbonate solution (20 mL), and saturated aqueous sodium carbonate solution (10 mL). The layers were separated, and the aqueous layer was extracted with additional 10% 2-propanol/chloroform (2×10 mL). The combined organics were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (1-5% methanol/dichloromethane, linear gradient) to afford 5-methylthieno[2,3-c]pyridin-7-amine. MS ESI calc'd. for C8H9N2S [M+H]+ 165. found 165. 1H NMR (500 MHz, CDCl3) δ 7.54 (d, J=5.3 Hz, 1H), 7.23 (d, J=5.3 Hz, 1H), 7.03 (s, 1H), 4.66 (s, 2H), 2.49 (s, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionToluene was added to the flask
  3. concentrationthe reaction mixture was concentrated under reduced pressure again
  4. additionThe residue was diluted with 10% 2-propanol/chloroform (30 mL), saturated aqueous sodium bicarbonate solution (20 mL), and saturated aqueous sodium carbonate solution (10 mL)
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with additional 10% 2-propanol/chloroform (2×10 mL)
  7. washThe combined organics were washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by chromatography on silica gel (1-5% methanol/dichloromethane, linear gradient)

Sources & evidence

ORD record
ord-e2832b22054748a4bd60d45b71c3a3fe
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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