Sodium Hydroxide → HCID 21084001, compound

HRID 347925Notes

Reaction equation

HRID 347925 reaction equation
[CH3:1][C:2]1[N:3]([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:21](=[O:22])[CH:20]=[CH:19][C:18]4[C:23]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[C:24]([C:26]([O:28]CC)=[O:27])[S:25][C:17]3=4)=[CH:12][CH:11]=2)[CH:4]=[CH:5][N:6]=1.[OH-].[Na+]>CCO.O>[CH3:1][C:2]1[N:3]([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([N:16]3[C:21](=[O:22])[CH:20]=[CH:19][C:18]4[C:23]([C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=5)=[C:24]([C:26]([OH:28])=[O:27])[S:25][C:17]3=4)=[CH:14][CH:15]=2)[CH:4]=[CH:5][N:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21084055HCID 21084055, compound

Product 1

HCID 21084001HCID 21084001, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of the compound of Example 91 (134 mg, 0.27 mmol) in EtOH (0.5 mL) and water (0.73 mL) was added sodium hydroxide (0.27 mL of a 1M solution, 0.27 mmol) and the mixture heated at reflux for 5 h. The reaction was freeze dried to give 7-{4-[2-(2-Methyl-1H-imidazol-1-yl)ethoxy]phenyl}-6-oxo-3-phenyl-6,7-dihydrothieno[2,3-b]pyridine-2-carboxylic acid as a solid. LCMS (ES+) RT 2.34 minutes, 472 (M+H)+. This compound was dissolved in DMF (2 mL) and thionyl chloride (30 μL, 0.405 mmol) was added and the reaction stirred at r.t. for 5 mins. Aqueous ammonia (2 mL of a 25% solution) was added and the reaction stirred for 30 mins. The reaction was diluted with water (20 mL) and extracted with EtOAc (3×30 mL). The combined EtOAc extracts were washed with water (2×10 mL), brine (20 mL), dried (MgSO4) and concentrated in vacuo to give the title compound as a solid (104 mg, 82%). δH (CDCl3) 7.52–7.48 (3H, m), 7.37–7.33 (2H, m), 7.29–7.26 (2H, m), 7.20–7.18 (1H, m), 7.01–6.96 (3H, m), 6.90–6.88 (2H, m), 6.50 (1H, d, J 9.6 Hz), 4.23–4.20 (4H, m), 2.42 (3H, s). LCMS (ES+) RT 2.28 minutes, 471 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 h
  3. customdried

Sources & evidence

ORD record
ord-27c7f0fb3be443aa8e61d239e9722d2b
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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