Trimethylsilyl iodide → 5-(3-Aminomethyl-cyclohexyl)-3-methyl-5h-2-oxa-1,5,6-triaza-cyclopenta[a]naphthalen-4-one hydroiodide

HRID 1823269ノート

反応式

HRID 1823269 の反応式
C(OC(=O)[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([N:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][N:26]=3)[C:21]3=[N:28][O:29][C:30]([CH3:31])=[C:20]3[C:19]2=[O:32])[CH2:13]1)C1C=CC=CC=1.[I:34][Si](C)(C)C>ClCCl>[IH:34].[NH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([N:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][N:26]=3)[C:21]3=[N:28][O:29][C:30]([CH3:31])=[C:20]3[C:19]2=[O:32])[CH2:13]1

参加物

4

反応物 2

HCID 85247Trimethylsilyl iodideHCID 69652675[3-(3-Methyl-4-oxo-5H-2-oxa-1,5,6-triaza-cyclopenta-[a]naphthalen-5-yl)-cyclohexylmethyl]-carbamic acid benzyl ester

生成物 1

HCID 221701525-(3-Aminomethyl-cyclohexyl)-3-methyl-5h-2-oxa-1,5,6-triaza-cyclopenta[a]naphthalen-4-one hydroiodide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Dissolve [3-(3-methyl-4-oxo-5H-2-oxa-1,5,6-triaza-cyclopenta-[a]naphthalen-5yl)-cyclohexylmethyl]-carbamic acid benzyl ester (0.52 g, 0.0012 mol) in dry dichloromethane and cool in an ice bath under nitrogen. Add iodotrimethylsilane (0.50 mL, 0.0035 mol) and stir overnight while warming to ambient temperature. Quench the mixture with methanol (approx. 5 mL) and concentrate in vacuo. Take up the resulting residue in minimal dichloromethane and add diethyl ether. Concentrate and titrate from dichloromethane/diethyl ether to give a dark solid. Decant the solvent and dry the solid in vacuo to give a near quantitative yield of the crude amine salt as a dark solid. Use directly without purification. MS(ES): (M+1)+ 313.2, 314.2 m/z.

後処理

  1. temperaturecool in an ice bath under nitrogen
  2. customQuench the mixture with methanol (approx. 5 mL)
  3. concentrationconcentrate in vacuo
  4. additionadd diethyl ether
  5. concentrationConcentrate
  6. customtitrate from dichloromethane/diethyl ether to give a dark solid
  7. customDecant the solvent
  8. customdry the solid in vacuo

出典と根拠

ORDレコード
ord-fa42a99d8571436ea144b04400a2c31e
出典データセット
uspto-grants-2006_05
特許番号
US07037921B2

反応ノート

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