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Methylamine → N-(1-{2,6-dichloro-4-[(methylamino)methyl]benzoyl}-1H-pyrrolo[3,2-c]pyridin-4-yl)cyclopropanecarboxamide

HRID 875497
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인쇄 미리보기

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HRID 875497 반응식
Br[CH2:2][C:3]1[CH:25]=[C:24]([Cl:26])[C:6]([C:7]([N:9]2[C:17]3[CH:16]=[CH:15][N:14]=[C:13]([NH:18][C:19]([CH:21]4[CH2:23][CH2:22]4)=[O:20])[C:12]=3[CH:11]=[CH:10]2)=[O:8])=[C:5]([Cl:27])[CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:34][NH2:35]>C(#N)C>[Cl:26][C:24]1[CH:25]=[C:3]([CH2:2][NH:35][CH3:34])[CH:4]=[C:5]([Cl:27])[C:6]=1[C:7]([N:9]1[C:17]2[CH:16]=[CH:15][N:14]=[C:13]([NH:18][C:19]([CH:21]3[CH2:23][CH2:22]3)=[O:20])[C:12]=2[CH:11]=[CH:10]1)=[O:8]
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5

반응물 3

HCID 6329MethylamineHCID 10796Cesium carbonateHCID 86720669N-{1-[4-(bromomethyl)-2,6-dichlorobenzoyl]-1H-pyrrolo[3,2-c]pyridin-4-yl}cyclopropanecarboxamide

생성물 1

HCID 71061823N-(1-{2,6-dichloro-4-[(methylamino)methyl]benzoyl}-1H-pyrrolo[3,2-c]pyridin-4-yl)cyclopropanecarboxamide수율 61.6%

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

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온도
0 °C

실험 절차

A solution of N-{1-[4-(bromomethyl)-2,6-dichlorobenzoyl]-1H-pyrrolo[3,2-c]pyridin-4-yl}cyclopropanecarboxamide (50 mg, 0.107 mmol) in acetonitrile was treated with cesium carbonate (69.74 mg, 0.2140 mmol) and stirred for about 15 minutes. The mixture was cooled to 0° C. followed by the portion wise addition of methyl amine (10.68 mg, 0.16 mmol). The reaction mixture was then stirred at room temperature for about 20 minutes and concentrated under vacuum, followed by addition of ice cold water to give N-(1-{2,6-dichloro-4-[(methylamino)methyl]benzoyl}-1H-pyrrolo[3,2-c]pyridin-4-yl)cyclopropanecarboxamide (27.5 mg) as white solid.

후처리

  1. stirringThe reaction mixture was then stirred at room temperature for about 20 minutes
  2. concentrationconcentrated under vacuum
  3. additionfollowed by addition of ice cold water

출처 및 근거

ORD 기록
ord-aff10643fa9a4e92a634826d703b7563
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08980911B2

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