Isopropylamine → 7-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-quinoline-8-carboxylic acid isopropylamide

HRID 245642노트

반응식

HRID 245642 반응식
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]3[O:26][C:25](=[O:27])[C:24]4[C:23]5[C:18](=[CH:19][CH:20]=[CH:21][N:22]=5)[CH:17]=[CH:16][C:15]=4[N:14]=3)=[CH:11][C:10]([C:28]([F:31])([F:30])[F:29])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.C(#N)C.O.[CH:36]([NH2:39])([CH3:38])[CH3:37]>[Cl-].[Na+].O>[CH:36]([NH:39][C:25]([C:24]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:28]([F:31])([F:29])[F:30])[CH:11]=2)=[O:26])=[CH:16][CH:17]=[C:18]2[C:23]=1[N:22]=[CH:21][CH:20]=[CH:19]2)=[O:27])([CH3:38])[CH3:37]

참가 물질

5

반응물 3

HCID 6363IsopropylamineHCID 18373917Acetonitrile--water (1/1)HCID 579901522-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-3-oxa-1,5-diaza-phenanthren-4-one

생성물 1

HCID 579901287-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-quinoline-8-carboxylic acid isopropylamide수율 71%

시약·촉매·용매 1

HCID 57417360Sodium chloride; water용매

실험 절차

To a suspension of 140 mg (0.28 mmol) of the above 2-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-3-oxa-1,5-diaza-phenanthren-4-one in 5.60 mL of a mixture acetonitrile: H2O 4:1 (v/v) is added 73 μL (0.85 mmol) of isopropylamine. The reaction mixture is stirred for 6 hours at ambient temperature. Brine is then added to the mixture and the product is extracted with ethyl acetate (3 times). The regrouped organic phases are dried on Na2SO4, filtrated and evaporated. The purification of the residue by flash chromatography (SiO2, heptane and ethyl acetate as eluants) affords 100 mg (70%) of a white solid; LC/MS: 503/505 (M+H)+, m.p.: 225-226° C.

후처리

  1. extractionthe product is extracted with ethyl acetate (3 times)
  2. customThe regrouped organic phases are dried on Na2SO4
  3. filtrationfiltrated
  4. customevaporated
  5. customThe purification of the residue by flash chromatography (SiO2, heptane and ethyl acetate as eluants)

출처 및 근거

ORD 기록
ord-7f99ff1e1b9f41c1b25b8779833180f7
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658801B2

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