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Pyridine → (R)-tert-butyl 1-(5-bromo-3-(cyclopropanecarboxamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-yl(methyl)carbamate hydrochloride

HRID 1034855
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HRID 1034855 반응식
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([Br:26])[C:9]=2[N:11]2[CH2:16][CH2:15][CH2:14][C@@H:13]([N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:12]2)[NH:4][CH:3]=1.N1C=CC=CC=1.[CH:33]1([C:36]([Cl:38])=[O:37])[CH2:35][CH2:34]1.O[Li].O>CN1C(=O)CCC1.CCOC(C)=O.CC#N.O>[ClH:38].[Br:26][C:8]1[C:9]([N:11]2[CH2:16][CH2:15][CH2:14][C@@H:13]([N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:12]2)=[C:10]2[C:2]([NH:1][C:36]([CH:33]3[CH2:35][CH2:34]3)=[O:37])=[CH:3][NH:4][C:5]2=[N:6][CH:7]=1
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참가 물질

8

반응물 4

HCID 1049PyridineHCID 77637Cyclopropanecarbonyl chlorideHCID 168937Lithium hydroxide, monohydrateHCID 67045616(R)-tert-butyl 1-(3-amino-5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-yl(methyl)carbamate

생성물 1

HCID 67045096(R)-tert-butyl 1-(5-bromo-3-(cyclopropanecarboxamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-yl(methyl)carbamate hydrochloride
수율 36%

시약·촉매·용매 3

HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매HCID 18373917Acetonitrile--water (1/1)용매

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온도
0 °C

실험 절차

A solution of (R)-tert-butyl 1-(3-amino-5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-yl(methyl)carbamate (305 mg, 0.7188 mmol) in NMP (3 mL) was cooled to 0° C. and pyridine (1.5 mL) was added. Then the mixture was treated dropwise with cyclopropanecarbonyl chloride (195.7 μL, 2.156 mmol) and stirred at 0° C. for 30 minutes. 2M LiOH.H2O (4 mL) was then added, and the mixture was stirred at room temperature. After 48 hours, the mixture was diluted with EtOAc (100 mL) and washed with water (3×20 mL). The organic layer was separated, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by reverse phase chromatography (Biotage SP4, C-18 40M+, 15-85% CH3CN/water, 35 CV) to provide (R)-tert-butyl 1-(5-bromo-3-(cyclopropanecarboxamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-yl(methyl)carbamate hydrochloride (127 mg, 36% yield) as a solid. LCMS (APCI+) m/z 492 (M+H)+.

후처리

  1. stirringthe mixture was stirred at room temperature
  2. waitAfter 48 hours
  3. washwashed with water (3×20 mL)
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by reverse phase chromatography (Biotage SP4

출처 및 근거

ORD 기록
ord-73eb26a94bca423eb161788640e11e6a
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08545897B2

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