Potassium Carbonate → (R)-tert-butyl 1-(3-(quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl)pyrrolidin-3-ylcarbamate

HRID 16001

반응식

HRID 16001 반응식
Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)[N:9]=[N:10][C:5]2=[N:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH:28]1[CH2:32][CH2:31][C@@H:30]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:29]1>CC(O)C>[N:18]1[C:19]2[C:14](=[CH:13][C:12]([CH2:11][N:8]3[C:6]4[C:5](=[N:4][CH:3]=[C:2]([N:28]5[CH2:32][CH2:31][C@@H:30]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:38])([CH3:37])[CH3:39])[CH2:29]5)[N:7]=4)[N:10]=[N:9]3)=[CH:21][CH:20]=2)[CH:15]=[CH:16][CH:17]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 547756086-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline

생성물 1

HCID 59341797(R)-tert-butyl 1-(3-(quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl)pyrrolidin-3-ylcarbamate수율 91.3%

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
80 °C

실험 절차

A mixture of 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (200 mg, 0.586 mmol), potassium carbonate (243 mg, 1.76 mmol), and (R)-tert-butyl pyrrolidin-3-ylcarbamate (218 mg, 1.17 mmol) in 2-propanol (6.0 mL) was heated in the microwave at 80° C. for 20 minutes. The mixture was allowed to cool and the solids were collected by filtration then purified by flash chromatography using a Horizon purification system eluting with chloroform/ethyl acetate (25-75%) to afford (R)-tert-butyl 1-(3-(quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl)pyrrolidin-3-ylcarbamate, (239 mg, 91%).

후처리

  1. temperatureto cool
  2. filtrationthe solids were collected by filtration
  3. customthen purified by flash chromatography
  4. customa Horizon purification system
  5. washeluting with chloroform/ethyl acetate (25-75%)

출처 및 근거

ORD 기록
ord-f8b1964c865546f980af44497f2bf07d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732604B2

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