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Oxalyl chloride → 3-(2-Fluoro-4-methylsulfanyl-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid (2-vinyloxy-ethoxy)-amide

HRID 1366797
ノート
印刷プレビュー

反応式

HRID 1366797 の反応式
[F:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11]1[C:15]2[CH:16]=[N:17][CH:18]=[CH:19][C:14]=2[S:13][C:12]=1[C:20](O)=[O:21].C(Cl)(=O)C(Cl)=O.[CH:29]([O:31][CH2:32][CH2:33][O:34][NH2:35])=[CH2:30].CCN(C(C)C)C(C)C>ClCCl.CN(C=O)C>[CH:29]([O:31][CH2:32][CH2:33][O:34][NH:35][C:20]([C:12]1[S:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][C:15]=2[C:11]=1[NH:10][C:3]1[CH:4]=[CH:5][C:6]([S:8][CH3:9])=[CH:7][C:2]=1[F:1])=[O:21])=[CH2:30]
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

7

反応物 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 21867017O-(2-(Vinyloxy)ethyl)hydroxylamineHCID 597039013-(2-Fluoro-4-methylsulfanyl-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid

生成物 1

HCID 597038883-(2-Fluoro-4-methylsulfanyl-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid (2-vinyloxy-ethoxy)-amide収率 18%

試薬・触媒・溶媒

2
HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

A suspension of 3-(2-fluoro-4-methylsulfanyl-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid (0.107 g, 0.32 mmol) in dry dichloromethane (5 ml) under an atmosphere of nitrogen was cooled to 0° C. and treated with DMF (1 drop) and oxalyl chloride (0.081 ml, 0.96 mmol). The reaction mixture was stirred for 1 hour then the solvent removed in vacuo. The resultant residue was re-suspended in dry dichloromethane (1 ml) and treated dropwise with a solution of O-(2-vinyloxy-ethyl) -hydroxylamine (0.066 g, 0.64 mmol) and DIPEA (0.167 ml, 0.96 mmol) in dry dichloromethane (4 ml) before being stirred for 18 hours. The reaction mixture was washed (water, brine), dried (MgSO4), filtered and concentrated in vacuo. The resultant residue was subjected to flash chromatography (Si-SPE, gradient 0-30% ethyl acetate in dichloromethane) to provide the title compound as a yellow solid (0.024 g, 18%). LCMS (method B): RT=3.17 min, M+H+ 420.

後処理

  1. customthe solvent removed in vacuo
  2. stirringbefore being stirred for 18 hours
  3. washThe reaction mixture was washed (water, brine)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-25a59f44cc0a45b19b79d5c6d7cc2410
出典データセット
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07893085B2

反応ノート

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