Acetic Acid → Tert-butyl 3-{7-(bis{[2-(trimethylsilyl)ethoxy]methyl}amino)-6-bromo-3-[6-(1-hydroxy-1-methylethyl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidin-5-yl}-8-azabicyclo[3.2.1]octane-8-carboxylate

HRID 589179노트

반응식

HRID 589179 반응식
[CH3:1][Si:2]([CH3:51])([CH3:50])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:42][O:43][CH2:44][CH2:45][Si:46]([CH3:49])([CH3:48])[CH3:47])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]([C:23]([OH:26])([CH3:25])[CH3:24])=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([CH:27]2[CH2:33][CH:32]3[N:34]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH:29]([CH2:30][CH2:31]3)[CH2:28]2)[CH:9]=1.C(O)(=O)C.[Br:56]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(OCC)(=O)C>[CH3:49][Si:46]([CH3:47])([CH3:48])[CH2:45][CH2:44][O:43][CH2:42][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:1])([CH3:50])[CH3:51])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]([C:23]([OH:26])([CH3:25])[CH3:24])=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([CH:27]2[CH2:33][CH:32]3[N:34]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH:29]([CH2:30][CH2:31]3)[CH2:28]2)[C:9]=1[Br:56]

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 67299289Tert-butyl 3-{7-(bis{[2-(trimethylsilyl)ethoxy]methyl}amino)-3-[6-(1-hydroxy-1-methylethyl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidin-5-yl}-8-azabicyclo[3.2.1]octane-8-carboxylate

생성물 1

HCID 68273121Tert-butyl 3-{7-(bis{[2-(trimethylsilyl)ethoxy]methyl}amino)-6-bromo-3-[6-(1-hydroxy-1-methylethyl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidin-5-yl}-8-azabicyclo[3.2.1]octane-8-carboxylate수율 99.5%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

tert-butyl 3-{7-(bis{[2-(trimethylsilyl)ethoxy]methyl}amino)-3-[6-(1-hydroxy-1-methylethyl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidin-5-yl}-8-azabicyclo[3.2.1]octane-8-carboxylate (0.500 g, 0.676 mmol) was dissolved in acetic acid (3.5 mL, 62 mmol) and N-bromosuccinimide (144.2 mg, 0.8105 mmol) was added in a single portion, and the reaction was monitored by HPLC. The reaction was complete in less than 10 min and the mixture was diluted with ethyl acetate and poured into a 1:1 mixture of saturated aq. sodium bicarbonate and aq. sodium thiosulfate (20%). The layers were separated and the organics washed several times with sodium bicarbonate solution then brine. The organics were dried with magnesium sulfate, filtered and concentrated to provide 550 mg of the desired material.

후처리

  1. waitThe reaction was complete in less than 10 min
  2. customThe layers were separated
  3. dry with materialThe organics were dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5e5afffb148b42a183d4e96f4e147250
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227971B2

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