Ammonium Chloride → N-[4-(4-Fluoro-2-methoxy-phenyl)-pyridin-3-yl]-3-methanesulfonyl-N-(2-methanesulfonyl-ethyl)-5-trifluoromethyl-benzamide

HRID 878355노트

반응식

HRID 878355 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[NH:14][CH2:15][CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])=[C:4]([O:21][CH3:22])[CH:3]=1.FC1C=CC=C(OC)C=1C1C=CN=CC=1N(CC(F)(F)F)[C:39](=[O:54])[C:40]1[CH:45]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:43]=[C:42]([S:50]([CH3:53])(=[O:52])=[O:51])[CH:41]=1.CCN(C(C)C)C(C)C.[NH4+].[Cl-]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:14]([CH2:15][CH2:16][S:17]([CH3:20])(=[O:18])=[O:19])[C:39](=[O:54])[C:40]2[CH:45]=[C:44]([C:46]([F:49])([F:47])[F:48])[CH:43]=[C:42]([S:50]([CH3:53])(=[O:52])=[O:51])[CH:41]=2)=[C:4]([O:21][CH3:22])[CH:3]=1

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 706632644-(4-fluoro-2-methoxyphenyl)-N-(2-(methylsulfonyl)ethyl)pyridin-3-amineHCID 86670807N-[4-(2-Fluoro-6-methoxy-phenyl)-pyridin-3-yl]-3-methanesulfonyl-N-(2,2,2-trifluoro-ethyl)-5-trifluoromethyl-benzamide2회

생성물 1

HCID 60196698N-[4-(4-Fluoro-2-methoxy-phenyl)-pyridin-3-yl]-3-methanesulfonyl-N-(2-methanesulfonyl-ethyl)-5-trifluoromethyl-benzamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 4-(4-fluoro-2-methoxyphenyl)-N-(2-(methylsulfonyl)ethyl)pyridin-3-amine (0.08 g, 247 μmol, example 192, intermediate a) and 3-(methylsulfonyl)-5-(trifluoromethyl)benzoyl chloride (177 mg, 617 μmol, example 223, intermediate d) in CH2Cl2 (2 mL) was added DIPEA (128 mg, 172 μL, 987 μmol) and the clear solution was stirred at room temperature for 19 hours. The reaction mixture was poured on saturated aqueous NH4Cl solution and CH2Cl2 and the layers were separated. The aqueous layer was extracted twice with CH2Cl2. The organic layers were dried over MgSO4, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 20 g column using a MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Light brown foam (0.075 g; 52%). MS (ESI): m/z=575.09 [M+H]+.

후처리

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted twice with CH2Cl2
  3. dry with materialThe organic layers were dried over MgSO4
  4. filtrationfiltered
  5. additiontreated with silica gel
  6. customevaporated
  7. customThe compound was purified by silica gel chromatography on a 20 g column
  8. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

출처 및 근거

ORD 기록
ord-fdc3733fe14e455580fba45e0be948a2
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987307B2

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