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Trifluoroacetic acid → HCID 69096290、化合物

HRID 1430440
ノート
印刷プレビュー

反応式

HRID 1430440 の反応式
COC1C=CC([CH2:7][N:8](C)[C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[C:14]([C:21]4[CH:26]=[C:25]([NH2:27])[C:24]([F:28])=[CH:23][C:22]=4[Cl:29])[C:15](=[O:20])[N:16]3[CH3:19])=[CH:11][N:10]=2)=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:27][C:25]1[C:24]([F:28])=[CH:23][C:22]([Cl:29])=[C:21]([C:14]2[C:15](=[O:20])[N:16]([CH3:19])[C:17]3[C:12]([CH:13]=2)=[CH:11][N:10]=[C:9]([NH:8][CH3:7])[CH:18]=3)[CH:26]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 69296325HCID 69296325、化合物

生成物 1

HCID 69096290HCID 69096290、化合物収率 72.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 7-((4-methoxybenzyl)(methyl)amino)-3-(5-amino-2-chloro-4-fluorophenyl)-1-methyl-1,6-naphthyridin-2(1H)-one (3 g, 6.6 mmol) in DCM (50 mL) was treated with TFA (20 mL) and the mixture was heated to reflux overnight. The mixture was concentrated under reduced pressure, the residue was dissolved in 10% HCl (50 mL), washed with EtOAc, neutralized with satd. NaHCO3 and extracted with EtOAc (3×). The combined organics were washed with brine, dried (Na2SO4) and concentrated in vacuo to give 3-(5-amino-2-chloro-4-fluorophenyl)-1-methyl-7-(methylamino)-1,6-naphthyridin-2(1H)-one (1.6 g, 72% yield) 1H NMR (300 MHz, DMSO-d6): δ 8.36 (s, 1H), 7.66 (s, 1H), 7.17 (d, J=10.8 Hz, 1H), 7.05 (m, 1H), 6.71 (d, J=9.6 Hz, 1), 6.15 (s, 1H), 5.30 (s, 2H), 3.47 (s, 3H), 3.42 (s, 1H), 2.84 (d, J=4.4 Hz, 3H); MS (ESI) m/z: 333.1 [M+H]+

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. concentrationThe mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in 10% HCl (50 mL)
  5. washwashed with EtOAc
  6. extractionNaHCO3 and extracted with EtOAc (3×)
  7. washThe combined organics were washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-24adf2d4479a4b0492c012c651232bb0
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08940756B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート