Ethanol → 3-((3-(1,1,2,2-Tetrafluoroethoxy)benzyl)(3-(4-aminophenoxy)phenyl)amino)-1,1,1-trifluoropropan-2-ol

HRID 990407노트

반응식

HRID 990407 반응식
[N+:1]([C:4]1[CH:38]=[CH:37][C:7]([O:8][C:9]2[CH:10]=[C:11]([N:15]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]([F:36])([F:35])[CH:32]([F:34])[F:33])[CH:25]=3)[CH2:16][CH:17]([OH:22])[C:18]([F:21])([F:20])[F:19])[CH:12]=[CH:13][CH:14]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H].[CH2:41](O)[CH3:42]>[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:10]=[C:11]([N:15]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]([F:35])([F:36])[CH:32]([F:33])[F:34])[CH:25]=3)[CH2:16][CH:17]([OH:22])[C:18]([F:21])([F:20])[F:19])[CH:12]=[CH:13][CH:14]=2)=[CH:37][CH:38]=1.[CH2:41]([NH:1][C:4]1[CH:38]=[CH:37][C:7]([O:8][C:9]2[CH:10]=[C:11]([N:15]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]([F:36])([F:35])[CH:32]([F:34])[F:33])[CH:25]=3)[CH2:16][CH:17]([OH:22])[C:18]([F:21])([F:20])[F:19])[CH:12]=[CH:13][CH:14]=2)=[CH:6][CH:5]=1)[CH3:42]

참가 물질

6

반응물 3

HCID 702EthanolHCID 111244671,1,1-Trifluoro-3-((3-(4-nitrophenoxy)phenyl)(3-(1,1,2,2-tetrafluoroethoxy)benzyl)amino)propan-2-olHCID 178418361HCID 178418361, 화합물

생성물 2

HCID 110818833-((3-(1,1,2,2-Tetrafluoroethoxy)benzyl)(3-(4-aminophenoxy)phenyl)amino)-1,1,1-trifluoropropan-2-olHCID 235060983-[[3-(4-(Ethylamino)phenoxy]phenyl][[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]amino]-1,1,1-trifluoro-2-propanol

시약·촉매·용매 1

HCID 23938Palladium촉매

실험 절차

A solution of 3-[[3-(4-nitrophenoxy)phenyl][[3-(1,1,2,2-tetrafluoroethoxy) phenyl]-methyl]amino]-1,1,1-trifluoro-2-propanol (33.8 mg, 0.06 mmol) in ethanol and 5% palladium on carbon (4 mL) was placed under 40 psi hydrogen gas for 7H. The mixture was filtered through celite, the solvent was evaporated, and the residue was purified by silica gel chromatography eluting with 25% ethyl acetate in hexane to give 13.4 mg (42%) of (EX-450A) as 3-[[3(4-aminophenoxy)phenyl][[3-(1,1,2,2-tetrafluoroethoxy) phenyl]methyl]amino]-1,1,1-trifluoro-2-propanol and 13.9 mg (41%) of (EX-450B) as 3-[[3-[4-(ethylamino)phenoxy]phenyl][[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]amino]-1,1,1-trifluoro-2-propanol both as orange oils. 3-[[3-(4-aminophenoxy)phenyl][[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]-amino]-1,1,1-trifluoro-2-propanol: HRMS calcd. for C24H22F7N2)3: 519.1519 [M+H]+, found: 519.1529. 1H NMR (acetone-d6) δ3.63 (dd, 1H), 3.96 (dd, 1H), 4.42-4.58 (m, 1H), 4.80 (s, 2H), 5.88 (m, 1H), 6.20 (m, 1H), 6.32-6.77 (m, 6H), 6.92 (d, 1H), 7.06-7.26 (m, 3H), 7.43 (m, 1H). 3-[[3-[4-(ethylamino)phenoxyphenyl][[3-(1,1,2,2-tetrafluoroethoxy) phenyl]-methyl]amino]-1,1,1-trifluoro-2-propanol: HRMS calcd. for C26H26F7N2O3: 547.1832 [M+H]+. found: 547.1819. 1H NMR (acetone-d6) δ1.23 (t, 3H), 3.17 (q, 2H), 3.63 (dd, 1H), 3.96 (dd, 1H), 4.424.58 (m, 1H), 4.79 (s, 2H), 5.85 (d, 1H), 6.20 (m, 1H), 6.33 (m, 1H), 6.47 (m, 1H), 6.50 (tt, 1J), 6.61 (d, 2H), 6.78 (d, 2H), 7.09 (t, 1H), 7.20 (m, 1H), 7.23 (d, 1H), 7.42 (m, 1H).

후처리

  1. filtrationThe mixture was filtered through celite
  2. customthe solvent was evaporated
  3. customthe residue was purified by silica gel chromatography
  4. washeluting with 25% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-3bdc39b8c35748f986ed396b4224efea
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06458803B1

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