1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-(6-quinolinyloxy)-N-(1-tert-butyldimethylsilyloxy-4-methylpent-2-yn-4-yl)butyramide

HRID 1244804ノート

反応式

HRID 1244804 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH:12]([CH2:16][CH3:17])[C:13]([OH:15])=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH2:18][C:19]([CH3:32])([CH3:31])[C:20]#[C:21][CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25].Cl.CN(C)CCCN=C=NCC.CCCCCC.C(OCC)(=O)C>CN(C)C1C=CN=CC=1.ClCCl>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH:12]([CH2:16][CH3:17])[C:13]([NH:18][C:19]([CH3:32])([CH3:31])[C:20]#[C:21][CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:25])[CH3:26])=[O:15])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

参加物

7

反応物 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21226206Ethyl acetate hexaneHCID 219231162-(6-Quinolinyloxy)butyric acidHCID 219231344-Amino-1-tert-butyldimethylsilyloxy-4-methylpent-2-yne

生成物 1

HCID 219231372-(6-quinolinyloxy)-N-(1-tert-butyldimethylsilyloxy-4-methylpent-2-yn-4-yl)butyramide収率 10.9%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

2-(6-Quinolinyloxy)butyric acid (0.61 g), 4-amino-1-tert-butyldimethylsilyloxy-4-methylpent-2-yne (0.57 g) and 4-dimethylaminopyridine (0.010 g) in dry dichloromethane (10 ml) were stirred and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.53 g) was added. The mixture was stirred at ambient temperature for 3.5 hours, stored for 2 days, diluted with dichloromethane, washed with saturated aqueous sodium hydrogen carbonate (twice) and then with water. The organic phase was dried over magnesium sulphate and evaporated under reduced pressure to give a yellow oil. The oil was fractionated by chromatography (silica; hexane/ethyl acetate, 3:1 by volume) to give a gum that was triturated with hexane to give the required product (0.12 g) as a colourless solid, m.p. 78–80° C.

後処理

  1. waitstored for 2 days
  2. washwashed with saturated aqueous sodium hydrogen carbonate (twice) and then with water
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customto give a yellow oil
  6. customto give a gum that
  7. customwas triturated with hexane

出典と根拠

ORDレコード
ord-3839cb092e7449049e20618601ebb118
出典データセット
uspto-grants-2006_10
特許番号
US07122672B2

反応ノート

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