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Tetrahydrofuran → 6-[5-(1-Amino-cyclopropyl)-pyridin-3-yl]-1-methyl-3,4-dihydro-1H-quinolin-2-one

HRID 1774814
ノート
印刷プレビュー

反応式

HRID 1774814 の反応式
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([C:18]4(C(O)=O)[CH2:20][CH2:19]4)[CH:15]=[N:16][CH:17]=3)=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1=[O:24].C1(P([N:39]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C1COCC1>C1(C)C=CC=CC=1>[NH2:39][C:18]1([C:14]2[CH:13]=[C:12]([C:8]3[CH:7]=[C:6]4[C:11](=[CH:10][CH:9]=3)[N:2]([CH3:1])[C:3](=[O:24])[CH2:4][CH2:5]4)[CH:17]=[N:16][CH:15]=2)[CH2:20][CH2:19]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 199401P,P-Diphenylphosphinic azideHCID 86679167HCID 86679167、化合物

生成物 1

HCID 715336316-[5-(1-Amino-cyclopropyl)-pyridin-3-yl]-1-methyl-3,4-dihydro-1H-quinolin-2-one収率 74.7%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

To solution of 1-(5-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)pyridin-3-yl)cyclopropanecarboxylic acid (0.551 g, 1.52 mmol) in toluene (20 mL) were added TEA (0.185 g, 1.83 mmol) and diphenylphosphoryl azide (0.419 g, 1.52 mmol) and then the reaction mixture was heated to reflux for 4 h. After cooling to 0° C., a 1 M solution of sodium trimethylsilanoate in THF (3.04 mL, 3.04 mmol) was added and the mixture was stirred for 45 min at room temperature. After quenching with 0.1 M aq. HCl (40 mL), the aqueous solution was washed with ether (2 times), then basified with 1 M aq. NaOH and then extracted with DCM (2×100 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and evaporated to dryness to give the title compound (0.333 g, 71%) as a yellow foam. MS: 294.4 (M+H+).

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 4 h
  3. customAfter quenching with 0.1 M aq. HCl (40 mL)
  4. washthe aqueous solution was washed with ether (2 times)
  5. extractionextracted with DCM (2×100 mL)
  6. washThe combined organics were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated to dryness

出典と根拠

ORDレコード
ord-ef25db3aead842bd8b39c2deb7fd9506
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09260408B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート