Hydrogen chloride-ethyl acetate → HCID 68672807, compound

HRID 2196079Notes

Reaction equation

HRID 2196079 reaction equation
[CH2:1](OC(=O)C)C.Cl.C[N:9]([CH2:17][CH2:18][N:19]([CH2:41][C:42]1[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=1)[CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:40]=[CH:39][C:27]2[N:28]([CH3:38])[C:29](=[O:37])[C:30]([CH3:36])([CH3:35])[C:31](=[O:34])[N:32]([CH3:33])[C:26]=2[CH:25]=1)C(=O)OC(C)(C)C>C(OCC)(=O)C>[CH3:38][N:28]1[C:29](=[O:37])[C:30]([CH3:35])([CH3:36])[C:31](=[O:34])[N:32]([CH3:33])[C:26]2[CH:25]=[C:24]([O:23][CH2:22][CH2:21][CH2:20][N:19]([CH2:18][CH:17]([NH2:9])[CH3:1])[CH2:41][C:42]3[CH:43]=[CH:44][N:45]=[CH:46][CH:47]=3)[CH:40]=[CH:39][C:27]1=2

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 68672860HCID 68672860, compound

Product 1

HCID 68672807HCID 68672807, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 4N-hydrogen chloride ethyl acetate solution (3.2 ml) was added to an ethyl acetate solution (30 ml) of tert-butyl methyl-(2-{pyridin-4-ylmethyl-[3-(1,3,3,5-tetramethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yloxy)propyl]amino}ethyl)carbamate (1.43 g, 2.5 mmol) and stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane, and trifluoroacetic acid (3 ml) was added thereto. Stirring was conducted at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in a dichloromethane-methanol mixture solvent. Polymer-bonded quaternary ammonium carbonate (PL-HcO3MP) was added thereto to neutralize the mixture. The resulting reaction mixture was filtered. The filtrate was concentrated under reduced pressure to thereby obtain 1.44 g (yield: quantitative) of 1,3,3,5-tetramethyl-7-{3-[(2-methyl aminoethyl)pyridin-4-ylmethylamino]propoxy}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione as a pale brown oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane
  3. additiontrifluoroacetic acid (3 ml) was added
  4. stirringStirring
  5. waitwas conducted at room temperature for 1 hour
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. dissolutionthe residue was dissolved in a dichloromethane-methanol mixture solvent
  8. additionPolymer-bonded quaternary ammonium carbonate (PL-HcO3MP) was added
  9. customThe resulting reaction mixture
  10. filtrationwas filtered
  11. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0594ec42c00b443daa7da75f6fe9d53c
Source dataset
uspto-grants-2012_12
Patent number
US08338406B2

Reaction notes

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