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 335248Notes

Reaction equation

HRID 335248 reaction equation
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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-bb20fddadd334bc69da2446835afe0fd
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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