Hydrochloric Acid → 6-[1-(2-Amino-ethyl)-1,2,3,4-tetrahydro-[1,7]naphthyridin-5-yl]-1-methyl-3,4-dihydro-1H-quinolin-2-one hydrochloride

HRID 530352Notes

Reaction equation

HRID 530352 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][N:10]1[C:19]2[C:14](=[C:15]([C:20]3[CH:21]=[C:22]4[C:27](=[CH:28][CH:29]=3)[N:26]([CH3:30])[C:25](=[O:31])[CH2:24][CH2:23]4)[CH:16]=[N:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)(C)(C)C.[ClH:33].O1CCOCC1>CO>[ClH:33].[NH2:7][CH2:8][CH2:9][N:10]1[C:19]2[C:14](=[C:15]([C:20]3[CH:21]=[C:22]4[C:27](=[CH:28][CH:29]=3)[N:26]([CH3:30])[C:25](=[O:31])[CH2:24][CH2:23]4)[CH:16]=[N:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 71536484{2-[5-(1-Methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-3,4-dihydro-2H-[1,7]naphthyridin-1-yl]-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 715364856-[1-(2-Amino-ethyl)-1,2,3,4-tetrahydro-[1,7]naphthyridin-5-yl]-1-methyl-3,4-dihydro-1H-quinolin-2-one hydrochlorideYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of {2-[5-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-3,4-dihydro-2H-[1,7]naphthyridin-1-yl]-ethyl}-carbamic acid tert-butyl ester (example 11, 0.06 g, 0.137 mmol) in MeOH (1 mL) was added 4M HCl in dioxane (0.137 mL, 0.550 mmol) and the reaction mixture was stirred at room temperature over night. Then, the reaction mixture was evaporated to dryness and the solid residue was triturated in diethyl ether, filtered off and further dried on the high vacuum to give the title compound (0.040 g, 70%) as an orange solid. MS: 337.3 (M+H+).

Workup

  1. customThen, the reaction mixture was evaporated to dryness
  2. customthe solid residue was triturated in diethyl ether
  3. filtrationfiltered off
  4. customfurther dried on the high vacuum

Sources & evidence

ORD record
ord-8608147ea0bd4f0d8a3c470239f9ef9e
Source dataset
uspto-grants-2016_05
Patent number
US09353081B2

Reaction notes

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