Ammonium Chloride → (-)-2-(1-ethyl-1H-pyrazol-4-yl)-9-hydroxy-9-trifluoromethyl-9H-fluorene-4-carboxamide

HRID 1799019노트

반응식

HRID 1799019 반응식
C(N1[CH:7]=[C:6]([C:8]2[CH:20]=[C:19]([C:21](O)=O)[C:18]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11]([OH:28])([C:24]([F:27])([F:26])[F:25])[C:10]=3[CH:9]=2)[CH:5]=[N:4]1)C.Cl.CN(C)[CH2:32][CH2:33]CN=C=NCC.[OH2:41].O[N:43]1C2C=CC=CC=2N=N1.[Cl-].[NH4+:53]>C(OCC)(=O)C.C(N(CC)CC)C.CN(C)C=O>[CH2:32]([N:53]1[CH:7]=[C:6]([C:8]2[CH:20]=[C:19]([C:21]([NH2:43])=[O:41])[C:18]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11]([OH:28])([C:24]([F:25])([F:27])[F:26])[C:10]=3[CH:9]=2)[CH:5]=[N:4]1)[CH3:33]

참가 물질

8

반응물 4

HCID 25517Ammonium ChlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 594931002-(1-ethyl-1H-pyrazol-4-yl)-9-hydroxy-9-trifluoromethyl-9H-fluorene-4-carboxylic acid

생성물 1

HCID 46191680(-)-2-(1-ethyl-1H-pyrazol-4-yl)-9-hydroxy-9-trifluoromethyl-9H-fluorene-4-carboxamide수율 85%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of an optically active form (0.051 g) of 2-(1-ethyl-1H-pyrazol-4-yl)-9-hydroxy-9-trifluoromethyl-9H-fluorene-4-carboxylic acid, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.038 g), 1-hydroxybenzotriazole hydrate (0.030 g), ammonium chloride (0.022 g) and dimethylformamide (1 ml) was added triethylamine (0.055 ml), and the mixture was stirred at room temperature overnight. To the reaction mixture was added ethyl acetate (10 ml), and the organic layer was successively washed once with hydrochloric acid, once with water, twice with saturated aqueous sodium hydrogen carbonate, 3 times with water and once with saturated brine. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give the title compound (0.043 g, 85%).

후처리

  1. washthe organic layer was successively washed once with hydrochloric acid, once with water, twice with saturated aqueous sodium hydrogen carbonate, 3 times with water and once with saturated brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d40adeba5ec84be1a01acbbb6d994a33
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343994B2

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