Trifluoroacetic acid → 3-chloro-5-[(6-chloro-2-fluoro-3-{[6-(methyloxy)-1-oxo-1,3,4,9-tetrahydro-2H-beta-carbolin-2-yl]methyl}phenyl)oxy]benzonitrile

HRID 1874793노트

반응식

HRID 1874793 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:21][CH2:20][C:19]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([O:22][CH3:23])[CH:17]=4)[N:12](C(OC(C)(C)C)=O)[C:11]=3[C:10]2=[O:31])=[C:4]([F:32])[C:3]=1[O:33][C:34]1[CH:39]=[C:38]([C:40]#[N:41])[CH:37]=[C:36]([Cl:42])[CH:35]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:42][C:36]1[CH:37]=[C:38]([CH:39]=[C:34]([O:33][C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[C:5]([CH2:8][N:9]3[CH2:21][CH2:20][C:19]4[C:18]5[C:13](=[CH:14][CH:15]=[C:16]([O:22][CH3:23])[CH:17]=5)[NH:12][C:11]=4[C:10]3=[O:31])[C:4]=2[F:32])[CH:35]=1)[C:40]#[N:41]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 594515721,1-Dimethylethyl 2-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-6-(methyloxy)-1-oxo-1,2,3,4-tetrahydro-9H-beta-carboline-9-carboxylate

생성물 1

HCID 594513583-chloro-5-[(6-chloro-2-fluoro-3-{[6-(methyloxy)-1-oxo-1,3,4,9-tetrahydro-2H-beta-carbolin-2-yl]methyl}phenyl)oxy]benzonitrile수율 80%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

1,1-Dimethylethyl 2-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-6-(methyloxy)-1-oxo-1,2,3,4-tetrahydro-9H-β-carboline-9-carboxylate (0.03 g, 0.05 mmol), was dissolved in CH2Cl2 (1.0 mL) and TFA (1.0 mL) was added dropwise. The reaction mixture was stirred 1 h and the solvent was evaporated. Purification was accomplished by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA). The desired fractions were neutralized with saturated NaHCO3 and extracted with EtOAc. The organic extracts were combined, dried over Na2SO4, filtered and evaporated to afford the title compound (0.02 g, 80%) as a tan solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.50 (br. s., 1H), 7.80 (s, 1H), 7.47-7.55 (m, 3H), 7.39 (t, 1H), 7.27 (d, 1H), 7.04 (d, 1H), 6.86 (dd, 1H), 4.76 (s, 2H), 3.75 (s, 3H), 3.66 (t, 2H), 2.97 (t, 2H). MS: m/z 510.2 (M+1).

후처리

  1. customthe solvent was evaporated
  2. customPurification
  3. extractionextracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-3c91a4a12c9a45128a1b6638d0880f7a
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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