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Cyclopropanecarbonyl chloride → N'-(Cyclopropylcarbonyl)-1-ethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazide

HRID 490886
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HRID 490886 반응식
Cl.Cl.[CH2:3]([N:5]1[C:9]2=[N:10][CH:11]=[C:12]([C:21]([NH:23][NH2:24])=[O:22])[C:13]([NH:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[C:8]2[CH:7]=[N:6]1)[CH3:4].CCN(C(C)C)C(C)C.[CH:34]1([C:37](Cl)=[O:38])[CH2:36][CH2:35]1>C1COCC1>[CH:34]1([C:37]([NH:24][NH:23][C:21]([C:12]2[C:13]([NH:14][CH:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)=[C:8]3[CH:7]=[N:6][N:5]([CH2:3][CH3:4])[C:9]3=[N:10][CH:11]=2)=[O:22])=[O:38])[CH2:36][CH2:35]1
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참가 물질

5

반응물 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 534878281-Ethyl-4-((tetrahydro-2H-pyran-4-yl)amino)-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazide dihydrochloride

생성물 1

HCID 57675148N'-(Cyclopropylcarbonyl)-1-ethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazide수율 45%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

A solution of Intermediate 19 (0.045 g) in THF (2 ml) was treated with DIPEA (0.045 ml), then with cyclopropylcarbonyl chloride (0.013 g) and stirred at room temperature for 16 h. The mixture was concentrated in vacuo and the residue partitioned between dichloromethane and water. The layers were separated and the organic layer concentrated in vacuo, then applied to an SPE cartridge (aminopropyl, 1 g). The column was eluted with methanol to afford Intermediate 20 as a white solid (0.02 g). LCMS showed MH+=373; TRET=2.15 min.

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue partitioned between dichloromethane and water
  3. customThe layers were separated
  4. concentrationthe organic layer concentrated in vacuo
  5. washThe column was eluted with methanol

출처 및 근거

ORD 기록
ord-5644c95b75ba4d8da6d565b0e8131feb
출처 데이터셋
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07528148B2

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