Hydrochloric Acid → isopropyl ((2S,4R)-1-acetyl-6-(4-((2-aminoethyl)carbamoyl)phenyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)carbamate hydrochloride

HRID 882271Notes

Reaction equation

HRID 882271 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([NH:22][CH2:23][CH2:24][NH:25]C(OC(C)(C)C)=O)=[O:21])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:33][C:34](=[O:39])[O:35][CH:36]([CH3:38])[CH3:37])[CH2:6][C@@H:5]1[CH3:40])(=[O:3])[CH3:2].[ClH:41]>O1CCOCC1>[ClH:41].[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:15]=[CH:16][C:17]([C:20](=[O:21])[NH:22][CH2:23][CH2:24][NH2:25])=[CH:18][CH:19]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:33][C:34](=[O:39])[O:35][CH:36]([CH3:37])[CH3:38])[CH2:6][C@@H:5]1[CH3:40])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 867094171-methylethyl {(2S,4R)-1-acetyl-6-[4-({[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]amino}carbonyl)phenyl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate

Product 1

HCID 71468505isopropyl ((2S,4R)-1-acetyl-6-(4-((2-aminoethyl)carbamoyl)phenyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)carbamate hydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 1-methylethyl {(2S,4R)-1-acetyl-6-[4-({[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]amino}carbonyl)phenyl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate (for a preparation see Intermediate 37)(90 mg, 0.163 mmol) in dioxane (2 ml) was treated with hydrogen chloride in 1,4-dioxane (4N, 2 mL, 8.00 mmol) and the resulting mixture stirred at room temperature for 5 h, then concentrated in vacuo. The resulting residue was triturated with Et2O and isolated by filtration to give isopropyl ((2S,4R)-1-acetyl-6-(4-((2-aminoethyl)carbamoyl)phenyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)carbamate hydrochloride (68 mg, 0.139 mmol, 85% yield) as a pale yellow solid. LCMS (HpH, 2 min), Rt=0.78 min.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resulting residue was triturated with Et2O
  3. customisolated by filtration

Sources & evidence

ORD record
ord-a96376431d874d12a10dcec441cd06b4
Source dataset
uspto-grants-2015_03
Patent number
US08993554B2

Reaction notes

Loading…