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Triethylamine → (R)-N-(4-(4-((1-(methylsulfonyl)pyrrolidin-3-yl)oxy)phenyl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide

HRID 873339
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HRID 873339 반응식
[NH:1]1[CH2:5][CH2:4][C@@H:3]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[C:14]4[N:15]([N:19]=[C:20]([NH:22][C:23]([CH:25]5[CH2:27][CH2:26]5)=[O:24])[CH:21]=4)[CH:16]=[CH:17][CH:18]=3)=[CH:9][CH:8]=2)[CH2:2]1.C(N(CC)CC)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>C(Cl)Cl>[CH3:35][S:36]([N:1]1[CH2:5][CH2:4][C@@H:3]([O:6][C:7]2[CH:8]=[CH:9][C:10]([C:13]3[C:14]4[N:15]([N:19]=[C:20]([NH:22][C:23]([CH:25]5[CH2:26][CH2:27]5)=[O:24])[CH:21]=4)[CH:16]=[CH:17][CH:18]=3)=[CH:11][CH:12]=2)[CH2:2]1)(=[O:38])=[O:37]
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HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 70979103(R)-N-(4-(4-(pyrrolidin-3-yloxy)phenyl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide

생성물 1

HCID 70979866(R)-N-(4-(4-((1-(methylsulfonyl)pyrrolidin-3-yl)oxy)phenyl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide수율 30%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

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온도
0 °C

실험 절차

(R)—N-(4-(4-(pyrrolidin-3-yloxy)phenyl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide (340 mg, 0.94 mmol) and triethylamine (0.16 ml, 1.13 mmol) were suspended in DCM (10 ml) and stirred at 0° C. under N2. Methane sulfonylchloride (77 μL, 0.99 mmol) was added slowly and the resulting solution was allowed to warm to room temperature over 4 h. The reaction mixture was washed with sat. NaHCO3 solution (aq.) and the aqueous phase extracted with DCM. The combined organics were dried (MgSO4), filtered, concentrated in vacuo and purified by preparative HPLC to give (R)—N-(4-(4-((1-(methylsulfonyl)pyrrolidin-3-yl)oxy)phenyl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide. (126 mg, 30% yield).

후처리

  1. temperatureto warm to room temperature over 4 h
  2. washThe reaction mixture was washed with sat. NaHCO3 solution (aq.)
  3. extractionthe aqueous phase extracted with DCM
  4. dry with materialThe combined organics were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-497bfc48b1254cfe8b72962b5ff305aa
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08975406B2

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