Methylamine → HCID 23019638, compound

HRID 1354199Notes

Reaction equation

HRID 1354199 reaction equation
Br[CH:2]([C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[CH:12][N:13]3[C:18]([C:19]=2[CH3:20])=[C:17]([CH:21]2[CH2:23][CH2:22]2)[CH:16]=[C:15]([C:24]([O:26]CC)=[O:25])[C:14]3=[O:29])[CH:7]=[CH:8][CH:9]=1)[CH3:3].[CH3:30][NH2:31]>O1CCCC1>[CH:21]1([C:17]2[CH:16]=[C:15]([C:24]([OH:26])=[O:25])[C:14](=[O:29])[N:13]3[C:18]=2[C:19]([CH3:20])=[C:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([CH:2]([NH:31][CH3:30])[CH3:3])[CH:5]=2)[CH:11]=[CH:12]3)[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 23019662HCID 23019662, compound

Product 1

HCID 23019638HCID 23019638, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

46.1 mg of ethyl 8-[3-(1-bromoethyl)phenyl]-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate was dissolved in 2 ml of tetrahydrofuran. 0.1 ml of a solution of 2.0 M of methylamine in tetrahydrofuran was added to the obtained solution and they were stirred for 10 hours. The reaction mixture was concentrated under reduced pressure, and the obtained residue was dissolved in 1 N hydrochloric acid. After washing the obtained solution with ethyl acetate, the aqueous layer was concentrated under reduced pressure. The obtained residue was dissolved in 2 ml of methanol. 1 ml of 1 N aqueous sodium hydroxide solution was added to the obtained solution, and they were stirred at 50° C. for 1 hour. The reaction mixture was made acidic with 1 N hydrochloric acid to obtain 8.1 mg of 1-cyclopropyl-9-methyl-8-[3-(1-methylaminoethyl)phenyl]-4-oxo-4H-quinolizine-3-carboxylic acid in the form of crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe obtained residue was dissolved in 1 N hydrochloric acid
  3. washAfter washing the obtained solution with ethyl acetate
  4. concentrationthe aqueous layer was concentrated under reduced pressure
  5. dissolutionThe obtained residue was dissolved in 2 ml of methanol
  6. addition1 ml of 1 N aqueous sodium hydroxide solution was added to the obtained solution, and they
  7. stirringwere stirred at 50° C. for 1 hour

Sources & evidence

ORD record
ord-bbd431f853cb4ef6a0b8d634356f2fa3
Source dataset
uspto-grants-2007_05
Patent number
US07223773B2

Reaction notes

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