Hydrochloric Acid → 1-((2S,4R)-4-amino-2-methyl-6-(5-(morpholine-4-carbonyl)pyridin-2-yl)-3,4-dihydroquinolin-1(2H)-yl)ethanone hydrochloride

HRID 882264Notes

Reaction equation

HRID 882264 reaction equation
[ClH:1].O1CCOCC1.[C:8]([N:11]1[C:20]2[C:15](=[CH:16][C:17]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)=[O:28])=[CH:23][N:22]=3)=[CH:18][CH:19]=2)[C@H:14]([NH:35]C(=O)OC(C)(C)C)[CH2:13][C@@H:12]1[CH3:43])(=[O:10])[CH3:9].CO>C(Cl)Cl>[ClH:1].[NH2:35][C@H:14]1[C:15]2[C:20](=[CH:19][CH:18]=[C:17]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)=[O:28])=[CH:23][N:22]=3)[CH:16]=2)[N:11]([C:8](=[O:10])[CH3:9])[C@@H:12]([CH3:43])[CH2:13]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 312751,4-DioxaneHCID 86709431tert-butyl ((2S,4R)-1-acetyl-2-methyl-6-(5-(morpholine-4-carbonyl)pyridin-2-yl)-1,2,3,4-tetrahydroquinolin-4-yl)carbamate

Product 1

HCID 867094321-((2S,4R)-4-amino-2-methyl-6-(5-(morpholine-4-carbonyl)pyridin-2-yl)-3,4-dihydroquinolin-1(2H)-yl)ethanone hydrochlorideYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4M hydrochloric acid in 1,4-dioxane (10.11 ml, 40.4 mmol) was added to tert-butyl ((2S,4R)-1-acetyl-2-methyl-6-(5-(morpholine-4-carbonyl)pyridin-2-yl)-1,2,3,4-tetrahydroquinolin-4-yl)carbamate (for a preparation, see Intermediate 64) (2 g, 4.04 mmol) at room temperature, followed by MeOH (10 mL) and DCM (10 mL) and the mixture stirred at room temperature for 2 mins. The mixture was concentrated in vacuo to give 1-((2S,4R)-4-amino-2-methyl-6-(5-(morpholine-4-carbonyl)pyridin-2-yl)-3,4-dihydroquinolin-1(2H)-yl)ethanone hydrochloride (1.60 g, 3.71 mmol, 92% yield).

Workup

  1. customfor a preparation
  2. customat room temperature
  3. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-09f23e6cb4984a118df16949f0867b2c
Source dataset
uspto-grants-2015_03
Patent number
US08993554B2

Reaction notes

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