Water → Ethyl 3,7-dimethyl-2-(morpholin-4-ylmethyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylate

HRID 2307306노트

반응식

HRID 2307306 반응식
[OH:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[S:13][C:14]([CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:15]([CH3:16])[C:3]=12.[C:24](=O)([O-])[O-].[K+].[K+].IC.O>CN(C=O)C>[CH3:16][C:15]1[C:3]2[C:2](=[O:1])[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]([CH3:24])[C:4]=2[S:13][C:14]=1[CH2:17][N:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178469718Ethyl 4-hydroxy-3-methyl-2-(morpholin-4-ylmethyl)thieno[2,3-b]pyridine-5-carboxylate

생성물 1

HCID 22605733Ethyl 3,7-dimethyl-2-(morpholin-4-ylmethyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylate수율 45.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Ethyl 4-hydroxy-3-methyl-2-(morpholin-4-ylmethyl)thieno[2,3-b]pyridine-5-carboxylate (Preparation 27, 1.47 g) and potassium carbonate (1.21 g) are suspended be in DMF (25 mL). The mixture is warmed until the ester dissolves and iodomethane (0.30 mL) is added. The reaction mixture is allowed to stir at room temperature for 20 h. The mixture is then poured into water (100 mL) and extracted with EtOAc (3×100 mL). The combined organic layers are washed with brine (2×25 mL), dried (Na2SO4), and partially concentrated. Hexanes are added and the resulting solid is filtered to afford 0.70 g of the title compound as a light yellow solids Physical characteristics. M.p. 172-173° C.; 1H NMR (400 MHz, DMSO-d6) δ 8.41, 4.19, 3.81, 3.65, 3.59, 2.48, 2.46, 1.27; MS (ESI+) m/z 351 (M+H)+. Anal. Found: C, 58.04; H, 6.54; N, 7.77; S, 8.97.

후처리

  1. dissolutiondissolves
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined organic layers are washed with brine (2×25 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationpartially concentrated
  6. additionHexanes are added
  7. filtrationthe resulting solid is filtered

출처 및 근거

ORD 기록
ord-a18c3904863e406ea1bd6cf759df9bd5
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06831081B2

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