Triethylamine → 3-(2,6-Dichloro-5-nitropyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane

HRID 75440

반응식

HRID 75440 반응식
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[C:4](Cl)[N:3]=1.Cl.[CH:14]12[O:21][CH:18]([CH2:19][CH2:20]1)[CH2:17][NH:16][CH2:15]2.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[N:3]=[C:4]([N:16]2[CH2:15][CH:14]3[O:21][CH:18]([CH2:19][CH2:20]3)[CH2:17]2)[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([Cl:8])[N:7]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 42978432,4,6-Trichloro-5-nitropyrimidineHCID 219835368-Oxa-3-aza-bicyclo(3.2.1)octane hydrochloride

생성물 1

HCID 866658963-(2,6-Dichloro-5-nitropyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

2,4,6-Trichloro-5-nitropyrimidine (45, 1.43 g, 6.26 mmoles) was dissolved in dichloromethane and cooled to 0° C. A solution of 8-oxa-3-azabicyclo[3.2.1]octane (2, 0.934 g, 6.26 mmoles) in dichloromethane and triethylamine (0.873 mL, 6.26 mmoles) was slowly added over 1 hour. The solution was allowed to stir at 0° C. for 2 hours, then warmed to room temperature and stirred for an additional 16 hours. The reaction mixture was filtered, the filtrate was concentrated, dissolved in ethyl acetate, washed with 1N hydrochloric acid, saturated sodium bicarbonate, brine, dried, and concentrated to provide 3-(2,6-dichloro-5-nitropyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane (46). Yield: 1.53 g (80%). HRMS; [M+H]+ Obs'd=305.0200, [M+H]+ Calc'd=305.0203.

후처리

  1. temperaturewarmed to room temperature
  2. stirringstirred for an additional 16 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. dissolutiondissolved in ethyl acetate
  6. washwashed with 1N hydrochloric acid, saturated sodium bicarbonate, brine
  7. customdried
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7de2637b233449baa3af76c79335ccfc
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835429B2

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