Ethylene Glycol → N-(1-Adamantylmethyl)-5-chloro-2-(2-hydroxyethoxy)isonicotinamide

HRID 1247601노트

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HRID 1247601 반응식
[H-].[Na+].[CH2:3]([OH:6])[CH2:4][OH:5].[C:7]12([CH2:17][NH:18][C:19](=[O:28])[C:20]3[C:25]([Cl:26])=[CH:24][N:23]=[C:22](Br)[CH:21]=3)[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH2:8]1)[CH2:14]2>CN1CCCC1=O>[C:7]12([CH2:17][NH:18][C:19](=[O:28])[C:20]3[C:25]([Cl:26])=[CH:24][N:23]=[C:22]([O:5][CH2:4][CH2:3][OH:6])[CH:21]=3)[CH2:8][CH:9]3[CH2:10][CH:11]([CH2:12][CH:13]([CH2:15]3)[CH2:14]1)[CH2:16]2

참가 물질

5

반응물 3

HCID 174Ethylene GlycolHCID 24758Sodium hydrideHCID 11773529N-(1-adamantylmethyl)-2-bromo-5-chloroisonicotinamide

생성물 1

HCID 11233863N-(1-Adamantylmethyl)-5-chloro-2-(2-hydroxyethoxy)isonicotinamide

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
150 °C

실험 절차

Sodium hydride (60%, 0.080 g) was added to ethylene glycol (3 ml) and the resulting suspension stirred under an atmosphere of nitrogen for 30 minutes. To this mixture was added a solution of N-(1-adamantylmethyl)-2-bromo-5-chloroisonicotinamide (Example 1(ii)) (0.192 g) in anhydrous N-methyl-2-pyrrolidinone (1 ml). The stirring bar was removed and the resulting solution heated in a MARS microwave for 15 minutes (300 Watts, 150° C.). The mixture was cooled and poured into water (50 ml) and extracted into is ethyl acetate (3×10 ml). The combined organic extracts were washed with brine (2×10 ml), dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel eluting with ethyl acetate:isohexane (1:1) to afford the sub-titled compound (0.092 g) as a white solid.

후처리

  1. customThe stirring bar was removed
  2. temperatureThe mixture was cooled
  3. additionpoured into water (50 ml)
  4. extractionextracted
  5. washThe combined organic extracts were washed with brine (2×10 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by chromatography on silica gel eluting with ethyl acetate:isohexane (1:1)

출처 및 근거

ORD 기록
ord-779672bb9afd47edbab7b0d1d89b13c8
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129246B2

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