Trimethylsilyl iodide → 5-(3-aminomethyl-cyclohexyl)-3-methyl-5H-2-oxa-1,5,8-triaza-cyclopenta[a]naphthalen-4-one hydroiodide

HRID 1823282Notes

Reaction equation

HRID 1823282 reaction equation
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][N:24]=[CH:25][CH: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][N:24]=[CH:25][CH:26]=3)[C:21]3=[N:28][O:29][C:30]([CH3:31])=[C:20]3[C:19]2=[O:32])[CH2:13]1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 69652685HCID 69652685, compound

Product 1

HCID 221701365-(3-aminomethyl-cyclohexyl)-3-methyl-5H-2-oxa-1,5,8-triaza-cyclopenta[a]naphthalen-4-one hydroiodide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve [3-(3-methyl-4-oxo-5H-2-oxa-1,5,8-triaza-cyclopenta[a]naphthalen-5-yl)-cyclohexylmethyl]-carbamic acid benzyl ester (0.45 g, 0.0010 mol) in dry dichloromethane (10 mL). add iodotrimethylsilane (0.36 mL, 0.0025 mol) and stir overnight at ambient temperature. Quench the mixture with methanol (5 mL) and concentrate in vacuo. Take up in minimal dichloromethane and add diethyl ether. Concentrate and titrate from dichloromethane/diethyl ether to form a dark solid. Decant he solvent and dry the solid in vacuo to give a near quantitative amount of the crude amine salt as a dark solid and is used directly without purification. MS(ES): (M+1)+ 313.2, 314.2 m/z.

Workup

  1. customQuench the mixture with methanol (5 mL)
  2. concentrationconcentrate in vacuo
  3. additionadd diethyl ether
  4. concentrationConcentrate
  5. customtitrate from dichloromethane/diethyl ether to form a dark solid
  6. customDecant he solvent
  7. customdry the solid in vacuo

Sources & evidence

ORD record
ord-f29d128316b34c0cae7180d505e76f6f
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

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