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Water → Ethanesulfonic acid [5-(7-fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-methyl-amide

HRID 1774846
ノート
印刷プレビュー

反応式

HRID 1774846 の反応式
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][C:3]=1[C:14]1[CH:15]=[C:16]([CH2:20][NH:21][S:22]([CH2:25][CH3:26])(=[O:24])=[O:23])[CH:17]=[N:18][CH:19]=1.[CH3:27]C(C)([O-])C.[K+].CI.O>CN(C=O)C>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][C:3]=1[C:14]1[CH:15]=[C:16]([CH2:20][N:21]([CH3:27])[S:22]([CH2:25][CH3:26])(=[O:24])=[O:23])[CH:17]=[N:18][CH:19]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 86679190Ethanesulfonic acid [5-(7-fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amide

生成物 1

HCID 86679193Ethanesulfonic acid [5-(7-fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-methyl-amide収率 60.9%

試薬・触媒・溶媒

1
HCID 6228Dimethylformamide溶媒

実験手順

To a solution of ethanesulfonic acid [5-(7-fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amide (example 16, 0.15 g, 0.39 mmol) in DMF (5 mL) was added potassium tert-butoxide (67.2 mg, 0.60 mmol) at 0° C. The resulting mixture was stirred for 30 minutes at 0° C. before methyl iodide (84.6 mg, 0.6 mmol) was added dropwise. After stirring for 2 hours, the mixture was treated with water, and extracted with EtOAc. The combined organic layers were then washed with water and brine in sequence, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was then purified by flash chromatography (silica gel, 5% methanol in dichloromethane) to afford the title compound (93 mg, 60%) as a white solid. MS: 392.1 (M+H+)+.

後処理

  1. additionwas added dropwise
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were then washed with water and brine in sequence
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was then purified by flash chromatography (silica gel, 5% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-4dd804ec201a44eb90056c3608eb2869
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実験手順後処理出典と根拠反応ノート