Hydrochloric Acid → HCID 22266529, compound

HRID 1994270Notes

Reaction equation

HRID 1994270 reaction equation
C(O)(=O)C.[NH2:5][C:6]1[C:7](=[O:20])[N:8]([CH2:16][CH2:17][CH2:18][CH3:19])[C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=2[CH:15]=1.[CH2:21]([N:28]=[C:29]=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:21]([NH:28][C:29]([NH:5][C:6]1[C:7](=[O:20])[N:8]([CH2:16][CH2:17][CH2:18][CH3:19])[C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=2[CH:15]=1)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 76639Benzyl isocyanateHCID 22266484HCID 22266484, compound

Product 1

HCID 22266529HCID 22266529, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

3-Amino-1-butyl-5,6,7,8-tetrahydro-1H-quinolin-2-one acetic acid salt (6-001-01) (5 mg, 0.018 mmol) was dissolved in methylene chloride (1 mL), and to the reaction mixture were added benzylisocyanate (2.5 μL, 0.02 mmol) and 4-dimethylaminopyridine (2.4 mg, 0.02 mmol), and the reaction mixture was stirred at room temperature for 4 h. To the reaction mixture was added diluted hydrochloric acid (0.1 mol/L, 3 mL), and the reaction mixture was extracted with ethyl acetate (10 mL), washed with brine (3 mL), dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (toluene/ethyl acetate) to give 1-benzyl-3-(1-butyl-2-oxo-1,2,5,6,7,8-hexahydroquinolin-3-yl)urea (6-005) (5.0 mg, 79%) as a white crystal.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate (10 mL)
  2. washwashed with brine (3 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (toluene/ethyl acetate)

Sources & evidence

ORD record
ord-7c02eeb896e64f95ae95263c83f045b7
Source dataset
uspto-grants-2010_01
Patent number
US07652141B2

Reaction notes

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