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

HRID 1455532노트

반응식

HRID 1455532 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매2회

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-e7a41b4342f046c6af4f4f06ac158f8c
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07482452B2

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