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 1874793ノート

反応式

HRID 1874793 の反応式
[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]

参加物

4

反応物 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

生成物 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]benzonitrile収率 80%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-3c91a4a12c9a45128a1b6638d0880f7a
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

反応ノート

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