1-Propanol → 6-Propoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid

HRID 639315

반응식

HRID 639315 반응식
C[O:2][C:3]([C:5]1[CH:10]=[N:9][C:8](Cl)=[C:7](Br)[N:6]=1)=[O:4].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:19]([OH:22])[CH2:20][CH3:21].[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1.[OH-].[K+]>CN(C=O)C.O>[CH2:19]([O:22][C:7]1[N:6]=[C:5]([C:3]([OH:2])=[O:4])[CH:10]=[N:9][C:8]=1[N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)[CH2:20][CH3:21]

참가 물질

8

반응물 5

HCID 10311-PropanolHCID 10796Cesium carbonateHCID 14797Potassium HydroxideHCID 31268PyrrolidineHCID 59254839Methyl 6-bromo-5-chloro-2-pyrazinecarboxylate

생성물 1

HCID 685674456-Propoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid수율 17.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

A mixture of 71.3 mg (0.28 mmol) 6-bromo-5-chloro-pyrazine-2-carboxylic acid methyl ester, 182.4 mg (0.56 mmol) Cs2CO3 and 17 mg (0.286 mmol) propanol in 1 mL DMF was heated to 60° C. for 16 h. Subsequently, 60 mg (0.84 mmol) pyrrolidine was added and the mixture was heated to 100° C. for 16 h. 0.2 mL water and 0.05 mL 5N KOH was added and heated to 60° C. for 2 h. The mixture was purified by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid. The combined product fractions were evaporated to yield 12 mg (17%) of the title compound. m/z (ES+): 252.0 (M+H).

후처리

  1. temperaturethe mixture was heated to 100° C. for 16 h
  2. temperatureheated to 60° C. for 2 h
  3. customThe mixture was purified by preparative HPLC on reversed phase
  4. washeluting with a gradient
  5. customformed from acetonitrile, water and formic acid
  6. customThe combined product fractions were evaporated

출처 및 근거

ORD 기록
ord-9f488e8a6de64466a386149e959d17ff
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691863B2

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