Methyl chloroformate → 1,2-Dihydro-3-methyl-1-[4-(methoxycarbonylamino)butan-1-yl]-1,4,7b-triazacyclopent[cd]inden-2-one

HRID 619454Notes

Reaction equation

HRID 619454 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[N:9]3[C:10](=[N:15][C:16]([CH3:17])=[C:8]3[C:7]1=[O:18])[CH:11]=[CH:12][CH:13]=2.C(N(CC)CC)C.[C:26](Cl)(=[O:29])[O:27][CH3:28]>C(Cl)Cl>[CH3:17][C:16]1[N:15]=[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[N:9]2[C:8]=1[C:7](=[O:18])[N:6]3[CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:26]([O:27][CH3:28])=[O:29]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 211902113-Methyl-1-[4-(amino)butan-1-yl]-1,4,7b-triazacyclopent[cd]inden-2-one

Product 1

HCID 211902651,2-Dihydro-3-methyl-1-[4-(methoxycarbonylamino)butan-1-yl]-1,4,7b-triazacyclopent[cd]inden-2-oneYield 78.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.22 g (5.0 mmol) of 1-[4-(amino) butan-1-yl]-1,2-dihydro-3-methyl-1,4,7b-triazacyclopent[cd]inden-2-one and 1.1 ml (7.9 mmol) of triethylamine in 40 ml of methylene chloride was added, while stirring under ice-cooling, 0.50 ml (6.5 mmol) of methyl chlorocarbonate. The mixture was stirred for 0.5 hour at room temperature. The reaction mixture was washed with an aqueous solution of sodium hydrogencarbonate, which was dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was recrystallized from methylene chloride-methanol-ether to give 1.192 g of the desired compound (78.9%, colorless crystals), m.p.175-176° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 0.5 hour at room temperature
  3. washThe reaction mixture was washed with an aqueous solution of sodium hydrogencarbonate, which
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was recrystallized from methylene chloride-methanol-ether

Sources & evidence

ORD record
ord-eaf2453b51ab4159ad4ce91b4a1f77fc
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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