Diisopropylethylamine → HCID 67441592, compound

HRID 2045656Notes

Reaction equation

HRID 2045656 reaction equation
Cl[S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]([CH3:22])([CH3:21])[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:23]([O:25][CH3:26])=[O:24])[CH:17]=3)[N:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Cl.CN.[CH:30]([N:33](CC)C(C)C)(C)C>ClCCl>[CH3:21][C:20]1([CH3:22])[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:23]([O:25][CH3:26])=[O:24])[CH:17]=2)[N:12]=[C:11]1[C:8]1[CH:9]=[CH:10][C:5]([S:2](=[O:4])(=[O:3])[NH:33][CH3:30])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 86658614HCID 86658614, compound

Product 1

HCID 67441592HCID 67441592, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a round bottom flask, a mixture of methyl 2-(4-(chlorosulfonyl)phenyl)-3,3-dimethyl-3,4-dihydroquinoline-6-carboxylate (396 mg, 1.0 mmol) in dichloromethane (10 mL) was added dropwise to a mixture of methylamine hydrochloride (68 mg, 1.0 mmol) and N,N-diisopropyl ethylamine (0.54 mL, 3.0 mmol) in dichloromethane (10 mL). The resultant mixture was allowed to stir at room temperature for 10 hours. The reaction mixture was washed by water several times, dried over anhydrous magnesium sulfate. Filtered and concentrated to provide methyl 3,3-dimethyl-2-(4-(N-methylsulfamoyl)phenyl)-3,4-dihydroquinoline-6-carboxylate as a yellow oil (190 mg). MS (ES+APCI) M+1=389.1.

Workup

  1. washThe reaction mixture was washed by water several times
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationFiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6809ab52c03643408d820d82a6591be6
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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