Potassium Hydroxide → 6-Oxo-7-phenyl-3-m-tolylamino-6,7-dihydrothieno[2,3-b]pyridine-2-carboxamide

HRID 1455532Notes

Reaction equation

HRID 1455532 reaction equation
[OH-:1].[K+].[O:3]=[C:4]1[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]2[S:16][C:17]([C:27]#[N:28])=[C:18]([NH:19][C:20]3[CH:21]=[C:22]([CH3:26])[CH:23]=[CH:24][CH:25]=3)[C:7]=2[CH:6]=[CH:5]1>O.CCO>[O:3]=[C:4]1[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]2[S:16][C:17]([C:27]([NH2:28])=[O:1])=[C:18]([NH:19][C:20]3[CH:21]=[C:22]([CH3:26])[CH:23]=[CH:24][CH:25]=3)[C:7]=2[CH:6]=[CH:5]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 116890016-Oxo-7-phenyl-3-m-tolylamino-6,7-dihydrothieno[2,3-b]pyridine-2-carbonitrile

Product 1

HCID 684564356-Oxo-7-phenyl-3-m-tolylamino-6,7-dihydrothieno[2,3-b]pyridine-2-carboxamideYield 141.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of KOH (12.69 g, 85+%) in water (230 ml) was added to a suspension of Example 23 (114 g) in EtOH (345 ml). The resulting mixture was heated at reflux for 70 minutes, by which time the reaction had gone to completion. It was cooled and water (285 ml) added. The suspension was filtered and washed with water (200 ml). The product was dried under vacuum to give the title compound as a yellow solid (120 g). δH (CDCl3) 8.90 (1H, s), 7.55-7.65 (3H, m), 7.40 (2H, m), 7.20-7.30 (2H, m), 6.90 (3H, m), 6.35 (1H, d, J 9 Hz), 5.40 (2H, br s), 3.70 (2H, q, EtOH), 2.35 (3H, s), 1.25 (3H, t, EtOH). LCMS (ES+) RT 3.1 minutes, 376 (M+H)+.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 70 minutes, by which time the reaction
  3. temperatureIt was cooled
  4. filtrationThe suspension was filtered
  5. washwashed with water (200 ml)
  6. customThe product was dried under vacuum

Sources & evidence

ORD record
ord-e7a41b4342f046c6af4f4f06ac158f8c
Source dataset
uspto-grants-2009_01
Patent number
US07482452B2

Reaction notes

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