Dimethylamine, hydrochloride → HCID 18333006, compound

HRID 2269748Notes

Reaction equation

HRID 2269748 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:21]=[C:20]2[C:15]([CH2:16][CH:17]([C:23](O)=[O:24])[C:18](=[O:22])[NH:19]2)=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:27][NH:28][CH3:29].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(#N)C.C1COCC1.O.C(N(CC)CC)C>[CH3:27][N:28]([CH3:29])[C:23]([CH:17]1[CH2:16][C:15]2[C:20](=[CH:21][C:12]([NH:11][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])=[CH:13][CH:14]=2)[NH:19][C:18]1=[O:22])=[O:24]

Participants

9

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 18333029HCID 18333029, compound

Product 1

HCID 18333006HCID 18333006, compoundYield 77.8%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 7-benzyloxycarbonylamino-2-oxo-1,2,3,4-tetrahydro-3-quinolinecarboxylic acid (7.0 g) in acetonitrile (80 ml) and THF (80 ml) were added dimethylamine hydrochloride (2.52 g), WSC(5.92 g), HOBt (3.15 g), and triethylamine (18 ml) subsequently at room temperature. The reaction mixture was stirred at room temperature for 10 hours, diluted with water, and extracted with combined solvent of ethyl acetate and THF. The organic layer was washed with 1N hydrochloric acid, water, saturated aqueous sodium hydrogencarbonate, water, saturated aqueous sodium chloride subsequently, dried, and concentrated. The precipitated crystals were washed with IPE to obtain the entitled compound (5.88 g).

Workup

  1. extractionextracted with combined solvent of ethyl acetate and THF
  2. washThe organic layer was washed with 1N hydrochloric acid, water, saturated aqueous sodium hydrogencarbonate, water, saturated aqueous sodium chloride subsequently
  3. customdried
  4. concentrationconcentrated
  5. washThe precipitated crystals were washed with IPE

Sources & evidence

ORD record
ord-8901ee8fdfe14a83b7e42c915b94654d
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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