Hydrochloric Acid → 3-(Phenylamino)-7-phenylthieno[2,3-b]pyridin-6(7h)-one

HRID 2358855

Reaction equation

HRID 2358855 reaction equation
[O:1]=[C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6]2[S:14][C:15](C([O-])=O)=[C:16]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:5]=2[CH:4]=[CH:3]1.[NH4+].Cl>O1CCOCC1.O>[C:18]1([NH:17][C:16]2[C:5]3[CH:4]=[CH:3][C:2](=[O:1])[N:7]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)[C:6]=3[S:14][CH:15]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66971000Ammonium 6-oxo-3-(phenylamino)-7-phenyl-6,7-dihydrothieno[2,3-b]pyridine-2-carboxylate

Product 1

HCID 684561183-(Phenylamino)-7-phenylthieno[2,3-b]pyridin-6(7h)-oneYield 53.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of the compound of Example 14 (200 mg) in 1,4-dioxan (10 mL) was added 2M HCl(aq) (0.5 mL) and the reaction mixture heated at 70° C. for 1 h. The reaction was diluted with water (30 mL), extracted with EtOAc (3×20 mL) and the EtOAc extracts dried (MgSO4) and concentrated in vacuo. The crude residue was purified by chromatography on silica (0-5% EtOAc in DCM) to give the title compound as a white solid (90 mg). δH (DMSO-d6) 8.21 (1H, bs), 7.96 (1H, d, J 9.6 Hz), 7.63-7.47 (3H, m), 7.43-7.36 (2H, m), 7.25-7.11 (2H, m), 7.10-7.03 (2H, m), 6.82-6.71 (1H, m), 6.46 (1H, d, J 9.6 Hz), 6.44 (1H, s). LCMS (ES+) RT 3.54 minutes, 319 (M+H)+.

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. dry with materialthe EtOAc extracts dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was purified by chromatography on silica (0-5% EtOAc in DCM)

Sources & evidence

ORD record
ord-ba2e3fbf3d764483947b99fefa30c51d
Source dataset
uspto-grants-2010_07
Patent number
US07763729B2

Linked notes

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