A-769662 → HCID 54689948, compound

HRID 1244119Notes

Reaction equation

HRID 1244119 reaction equation
[OH:1][C:2]1[C:3]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[OH:26])=[CH:16][CH:15]=3)=[CH:12][S:11][C:4]=2[NH:5][C:6](=[O:10])[C:7]=1C#N>OS(O)(=O)=O>[OH:1][C:2]1[C:3]2[C:13]([C:14]3[CH:15]=[CH:16][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[OH:26])=[CH:18][CH:19]=3)=[CH:12][S:11][C:4]=2[NH:5][C:6](=[O:10])[CH:7]=1

Participants

3

Reactant 1

HCID 54708532A-769662

Product 1

HCID 54689948HCID 54689948, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

4-hydroxy-3-(2′-hydroxy-1,1′-biphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile (0.040 g) in 40% H2SO4 (20 mL) was heated at reflux for 16 hours, cooled to room temperature and quenched with 50% NaOH (till pH=2). It was then extracted with ethyl acetate (3×70 mL), organic extracts washed with water (25 mL), brine (15 mL), concentrated and purified on a RP-HPLC system to afford the title compound. MS (ESI) m/e 334.0 (M−H)+; 1H NMR (400 MHz, DMSO-d6): δ ppm 10.96 (s, 1H), 9.52 (s, 1H), 7.53 (d, J=8.59, 2H), 7.47 (d, J=7.98, 2H), 7.29 (dd, J=7.67, 1.84, 1H), 7.16 (m, 1H), 7.04 (s, 1H), 6.96 (d, J=7.97, 1H), 6.89 (m, 1H), 5.76 (s, 1H).

Workup

  1. temperatureat reflux for 16 hours
  2. customquenched with 50% NaOH (till pH=2)
  3. extractionIt was then extracted with ethyl acetate (3×70 mL), organic extracts
  4. washwashed with water (25 mL), brine (15 mL)
  5. concentrationconcentrated
  6. custompurified on a RP-HPLC system

Sources & evidence

ORD record
ord-29636bc958f34bb8a7b5efea8fe1860f
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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