Hydrochloric Acid → 2-{[3-(aminomethyl)-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]oxy}-N-methylacetamide dihydrochloride

HRID 1986435Notes

Reaction equation

HRID 1986435 reaction equation
[CH2:1]([C:5]1[C:14]([CH2:15][NH:16]C(=O)OC(C)(C)C)=[C:13]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:31][CH2:32][C:33]([NH:35][CH3:36])=[O:34])[CH:11]=2)[N:6]=1)[CH:2]([CH3:4])[CH3:3].[ClH:37]>C(OCC)(=O)C>[ClH:37].[ClH:37].[NH2:16][CH2:15][C:14]1[C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[N:6][C:7]2[C:12]([C:13]=1[C:24]1[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=1)=[CH:11][C:10]([O:31][CH2:32][C:33]([NH:35][CH3:36])=[O:34])=[CH:9][CH:8]=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86605629Tert-butyl {[2-isobutyl-6-[2-(methylamino)-2-oxoethoxy]-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate

Product 1

HCID 688300382-{[3-(aminomethyl)-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]oxy}-N-methylacetamide dihydrochlorideYield 79%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of tert-butyl {[2-isobutyl-6-[2-(methylamino)-2-oxoethoxy]-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate (0.26 g, 0.53 mmol) in ethyl acetate (5 ml) was added 4N solution of hydrogen chloride in ethyl acetate (2 ml), and the mixture was stirred at room temperature for 3 hrs. The reaction mixture was concentrated under reduced pressure and crystallized from diisopropyl ether to give the title compound (0.20 g, yield 79%) as pale-yellow crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-8d696b0ce728492fad57489815b42591
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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