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

HRID 1823269노트

반응식

HRID 1823269 반응식
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

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fa42a99d8571436ea144b04400a2c31e
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07037921B2

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