Methylamine → N-methyl-1-(1-benzyloxycarbonylpiperidin-4-yl)-1H-indole-6-carboxamide

HRID 494914노트

반응식

HRID 494914 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]([OH:28])=O)[CH:24]=3)[CH:19]=[CH:18]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29](N1C=CN=C1)([N:31]1C=CN=C1)=O.CN>O1CCCC1>[CH3:29][NH:31][C:26]([C:23]1[CH:24]=[C:25]2[C:20]([CH:19]=[CH:18][N:17]2[CH:14]2[CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[CH2:16][CH2:15]2)=[CH:21][CH:22]=1)=[O:28]

참가 물질

5

반응물 3

HCID 6329MethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 576829061-(1-benzyloxycarbonylpiperidin-4-yl)-1H-indole-6-carboxylic acid

생성물 1

HCID 57682860N-methyl-1-(1-benzyloxycarbonylpiperidin-4-yl)-1H-indole-6-carboxamide수율 85.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2.00 g of 1-(1-benzyloxycarbonylpiperidin-4-yl)-1H-indole-6-carboxylic acid was dissolved in 20 ml of tetrahydrofuran, and 1.03 g of 1,1′-carbonylbis-1H-imidazole was then added thereto. The obtained mixture was stirred at room temperature for 1.5 hours, and 4.11 ml of a 40% methylamine aqueous solution was added thereto. After completion of the reaction, the reaction solution was extracted with ethyl acetate. The organic layer was washed with a saturated sodium bicarbonate aqueous solution, a saturated ammonium chloride aqueous solution, and a saturated sodium chloride solution. Thereafter, the organic layer was dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure, and the residue was then purified by NH silica gel column chromatography (ethyl acetate) and silica gel column chromatography (hexane/ethyl acetate), so as to obtain 1.77 g of the subject compound.

후처리

  1. customAfter completion of the reaction
  2. extractionthe reaction solution was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated sodium bicarbonate aqueous solution
  4. dry with materialThereafter, the organic layer was dried over anhydrous magnesium sulfate
  5. customAfter removing the drying agent
  6. filtrationby filtration
  7. concentrationthe organic layer was concentrated under a reduced pressure
  8. customthe residue was then purified by NH silica gel column chromatography (ethyl acetate) and silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-aa5b158d46d746b680ebfd50bfdfa376
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538123B2

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