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Potassium tert-butoxide → 1-(4-(2-(5-(3-Methylthieno[3,2-b]pyridin-7-ylthio)-3-phenoxypyridin-2-ylamino)thiazol-4-yl)piperidin-1-yl)ethanone

HRID 335248
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HRID 335248 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[C:8]([CH3:11])=[CH:9][S:10][C:3]=12.[C:12]([N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[N:22]=[C:23]([NH:26][C:27]3[N:32]=[CH:31][C:30]([S:33]CCC(OC)=O)=[CH:29][C:28]=3[O:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[S:24][CH:25]=2)[CH2:17][CH2:16]1)(=[O:14])[CH3:13].CC([O-])(C)C.[K+]>CS(C)=O>[CH3:11][C:8]1[C:4]2=[N:5][CH:6]=[CH:7][C:2]([S:33][C:30]3[CH:29]=[C:28]([O:40][C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[C:27]([NH:26][C:23]4[S:24][CH:25]=[C:21]([CH:18]5[CH2:19][CH2:20][N:15]([C:12](=[O:14])[CH3:13])[CH2:16][CH2:17]5)[N:22]=4)=[N:32][CH:31]=3)=[C:3]2[S:10][CH:9]=1
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참가 물질

5

반응물 3

HCID 23665647Potassium tert-butoxideHCID 574158647-Chloro-3-methylthieno(3,2-b)pyridineHCID 86631532Methyl 3-(6-(4-(1-acetylpiperidin-4-yl)thiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)propanoate

생성물 1

HCID 577427851-(4-(2-(5-(3-Methylthieno[3,2-b]pyridin-7-ylthio)-3-phenoxypyridin-2-ylamino)thiazol-4-yl)piperidin-1-yl)ethanone수율 44,690.102%

시약·촉매·용매 1

HCID 679
Dimethyl Sulfoxide
용매

실험 절차

7-chloro-3-methylthieno[3,2-b]pyridine (0.072 g, 0.39 mmol) and methyl 3-(6-(4-(1-acetylpiperidin-4-yl)thiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)propanoate (0.20 g, 0.39 mmol) were dissolved in DMSO (3 mL). The solution was degassed for 15 minutes under nitrogen. KOtBu (0.13 g, 1.2 mmol) was added and the reaction stirred at room temperature for two hours. The solution was quenched with water, extracted with dichloromethane, dried, and concentrated. Flash chromatography gave the title compound (0:100 g, 44% yield). 1H NMR (400 MHz, CDCl3) δ 1.60-1.72 (m, 2H), 2.03-2.09 (m, 2H), 2.11 (s, 31H), 2.51 (s, 3H), 2.66-2.73 (m, 1H), 2.83-2.90 (m, 1H), 3.15-3.22 (m, 1H), 3.88-3.94 (m, 1H), 4.70-4.73 (m, 1H), 6.51 (s, 1H), 6.75 (d, 1H), 7.05 (d, 2H), 7.17-7.25 (m, 2H), 7.36-7.40 (m, 3H), 8.30 (d, 1H), 8.48 (d, 1H), 8.84 (bs, 1H).

후처리

  1. customThe solution was degassed for 15 minutes under nitrogen
  2. customThe solution was quenched with water
  3. extractionextracted with dichloromethane
  4. customdried
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-bb20fddadd334bc69da2446835afe0fd
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08883828B2

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