Ethyl Acetate → HCID 89816262, 화합물

HRID 1500189노트

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HRID 1500189 반응식
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([C:13]2([C:32]([F:35])([F:34])[F:33])[CH2:17][CH2:16][N:15]([C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[CH:23]([NH:27][C:28](=[O:31])[CH2:29][CH3:30])[CH2:22][CH2:21]4)[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C([O:40]C(=O)C)C.C(=O)([O-])O.[Na+]>O.C(#N)C.FC(F)(F)C(O)=O.N1C=CC=CC=1C([O-])=O.[Ag+2].N1C=CC=CC=1C([O-])=O>[F:37][C:2]([F:36])([F:1])[C:3]1[CH:4]=[C:5]([C:13]2([C:32]([F:35])([F:34])[F:33])[CH2:17][CH2:16][N:15]([C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[CH:23]([NH:27][C:28](=[O:31])[CH2:29][CH3:30])[CH2:22][CH2:21]4)[CH:14]2[OH:40])[CH:6]=[C:7]([C:9]([F:10])([F:12])[F:11])[CH:8]=1

참가 물질

8

반응물 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 45377922N-[5-[3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl]indan-1-yl]propanamide

생성물 1

HCID 89816262HCID 89816262, 화합물수율 5.8%

시약·촉매·용매 4

HCID 178524371HCID 178524371, 화합물촉매HCID 962Water용매HCID 6342Acetonitrile용매HCID 6422Trifluoroacetic acid용매

실험 절차

131 mg (0.243 mmole) N-(5-{3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl}-2,3-dihydro-1H-inden-1-yl)propanamide (Ex. No. (II-a-963), known from WO 2010/043315, Table 6, Ex. No. 273) was dissolved in a solution of 0.6 ml water, 6 ml acetonitrile and 1.2 ml trifluoroacetic acid. At 0° C. 86 mg (0.243 mmole) silver-(II)2-pyridinecarboxylate were added in small portions until the solution has been discoloured. Immediately after decolourization ethylacetate and sodium hydrogencarbonate solution were added. The aqueous solution was extracted additionally two times with ethylacetate. The combined extracts were dried and evaporated under reduced pressure. The residue was purified by a reversed phase chromatography with a gradient acetonitrile/water to obtain 9 mg (5.8%) of the title compound as a mixture of isomers. NMR data are given for the main isomer.

후처리

  1. customAt 0° C
  2. extractionThe aqueous solution was extracted additionally two times with ethylacetate
  3. customThe combined extracts were dried
  4. customevaporated under reduced pressure
  5. customThe residue was purified by a reversed phase chromatography with a gradient acetonitrile/water

출처 및 근거

ORD 기록
ord-aff3313145be4865a6dddce188cf5f4a
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206122B2

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