Water → methyl 6-[(R)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]-4-trifluoromethylnicotinate

HRID 1811630

반응식

HRID 1811630 반응식
Cl.Cl.[C:3]1([C@H:13]([NH:15][C@@H:16]2[CH2:20][CH2:19][NH:18][CH2:17]2)[CH3:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.Cl[C:22]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][N:23]=1.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1.C(OCC)(=O)C>[C:3]1([C@H:13]([NH:15][C@@H:16]2[CH2:20][CH2:19][N:18]([C:22]3[CH:31]=[C:30]([C:32]([F:33])([F:35])[F:34])[C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][N:23]=3)[CH2:17]2)[CH3:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2775340Methyl 6-chloro-4-(trifluoromethyl)nicotinateHCID 67407230(R)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidine dihydrochloride

생성물 1

HCID 58973503methyl 6-[(R)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]-4-trifluoromethylnicotinate

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

To a solution of 157 mg of (R)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidine dihydrochloride and 120 mg of methyl 6-chloro-4-(trifluoromethyl)-nicotinate in 5 ml of dioxane was added 346 mg of potassium carbonate, and the reaction solution was stirred at 100° C. for 1 day. Further, to the reaction mixture was irradiated at 140° C. for 1 hour by using a Microwave reaction system, and then, the reaction mixture was cooled to room temperature. To the mixture were added water and ethyl acetate, and the mixture was stirred and the liquids were separated. The organic layer was dried and concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20→50:50), and then, purified by NH thin layer silica gel column chromatography (hexane:ethyl acetate=67:33) to obtain methyl 6-[(R)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]-4-trifluoromethylnicotinate (the following Table, Example, 12.001).

후처리

  1. customFurther, to the reaction mixture was irradiated at 140° C. for 1 hour
  2. customa Microwave reaction system
  3. temperaturethe reaction mixture was cooled to room temperature
  4. stirringthe mixture was stirred
  5. customthe liquids were separated
  6. customThe organic layer was dried
  7. concentrationconcentrated under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20→50:50)
  9. custompurified by NH thin layer silica gel column chromatography (hexane:ethyl acetate=67:33)

출처 및 근거

ORD 기록
ord-f9a3f14b311e4368874e34f445a40a39
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362274B2

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