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Ethyl isocyanate → N-[5-(3-{[(ethylamino)carbonyl]amino}phenyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide

HRID 18424
ノート
印刷プレビュー

反応式

HRID 18424 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[CH2:13][CH:12]([NH:17][S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])[CH2:11]3)[CH:5]=[CH:6][CH:7]=1.C(N(C(C)C)CC)(C)C.[CH2:33]([N:35]=[C:36]=[O:37])[CH3:34]>ClCCl>[CH2:33]([NH:35][C:36]([NH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[CH2:13][CH:12]([NH:17][S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])[CH2:11]3)[CH:5]=[CH:6][CH:7]=1)=[O:37])[CH3:34]
参加物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 8022Ethyl isocyanateHCID 81531DiisopropylethylamineHCID 46899970N-[5-(3-aminophenyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide

生成物 1

HCID 11538613N-[5-(3-{[(ethylamino)carbonyl]amino}phenyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide収率 24%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of Intermediate 4 (45 mg, 0.14 mmol), and diisopropylethylamine (36 mg, 0.28 mmol) in dry dichloromethane (3 ml) was cooled to 0° C. using an ice/methanol bath. Ethyl isocyanate (10 mg, 0.14 mmol) was added with stirring under argon and the whole mixture stirred at room temperature for 1 h. The reaction mixture was partitioned between dichloromethane (5 ml) and 1N hydrochloric acid (5 ml). The organic layer was removed and reduced to minimum volume under reduced pressure. The crude mixture was purified by flash column chromatography eluting from 0-50% ethyl acetate in 40-60° C. petroleum ether to give the title compound as a colourless oil (13 mg, 24%); mass spectrum (ES): Found 400 (ES−), C21H27N3O3S requires 401; 1H-NMR (400 MHz, CDCl3) δ 1.16 (3H, m), 1.38 (6H, m), 2.93 (2H, m), 3.19 (1H, m), 3.32 (4H, m), 4.32 (1H, m), 4.44 (1H, m), 4.82 (1H, m), 6.48 (1H, s), 7.23 (3H, m), 7.36 (3H, m), 7.54 (1H, m).

後処理

  1. stirringthe whole mixture stirred at room temperature for 1 h
  2. customThe reaction mixture was partitioned between dichloromethane (5 ml) and 1N hydrochloric acid (5 ml)
  3. customThe organic layer was removed
  4. customThe crude mixture was purified by flash column chromatography
  5. washeluting from 0-50% ethyl acetate in 40-60° C. petroleum ether

出典と根拠

ORDレコード
ord-c22f17ca4c5d479a94b1bba71baea5c6
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07741351B2

反応ノート

読み込み中…

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