Isopropylamine → 6-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-1H-indole-7-carboxylic acid isopropylamide

HRID 245606노트

반응식

HRID 245606 반응식
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]3[O:22][C:21](=[O:23])[C:20]4[C:15](=[CH:16][CH:17]=[C:18]5[CH:26]=[CH:25][NH:24][C:19]5=4)[N:14]=3)=[CH:11][C:10]([C:27]([F:30])([F:29])[F:28])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH:31]([NH2:34])([CH3:33])[CH3:32]>O1CCCC1>[CH:31]([NH:34][C:21]([C:20]1[C:15]([NH:14][C:13]([C:12]2[N:8]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=3)[N:9]=[C:10]([C:27]([F:29])([F:28])[F:30])[CH:11]=2)=[O:22])=[CH:16][CH:17]=[C:18]2[C:19]=1[NH:24][CH:25]=[CH:26]2)=[O:23])([CH3:33])[CH3:32]

참가 물질

4

반응물 2

HCID 6363IsopropylamineHCID 1361760267-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-1H-8-oxa-1,6-diaza-cyclopenta[a]naphthalen-9-one

생성물 1

HCID 579901666-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-1H-indole-7-carboxylic acid isopropylamide수율 16%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 110 mg (0.25 mmol) of the crude 7-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-1H-8-oxa-1,6-diaza-cyclopenta[a]naphthalen-9-one in 2.5 mL of anhydrous tetrahydrofuran, under Argon, is added 0.07 mL (0.77 mmol) of isopropylamine. The reaction is stirred during 5 hours at ambient temperature and then quenched with an aqueous saturated solution of ammonium chloride. The product is extracted twice with ethyl acetate and the combined organic phases are dried on Na2SO4, filtrated and the solvent is evaporated. After purification by flash chromatography on silica gel with hexanes and ethyl acetate as eluents and a preparative thin layer chromatography, 18.5 mg (0.04 mmol, 16%) of a white solid are obtained; LC/MS:513/515 (M+Na)+, m.p.: 240-242° C.

후처리

  1. customquenched with an aqueous saturated solution of ammonium chloride
  2. extractionThe product is extracted twice with ethyl acetate
  3. customthe combined organic phases are dried on Na2SO4
  4. filtrationfiltrated
  5. customthe solvent is evaporated
  6. customAfter purification by flash chromatography on silica gel with hexanes and ethyl acetate as eluents

출처 및 근거

ORD 기록
ord-2042812cf56f46dab18f4e8b1865964b
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658801B2

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