Hydrochloric Acid → 1-methylethyl [(2S,4R)-1-acetyl-6-(4-{2-[(2-aminoethyl)amino]-2-oxoethyl}phenyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate hydrochloride

HRID 882274Notes

Reaction equation

HRID 882274 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]([CH2:20][C:21]([NH:23][CH2:24][CH2:25][NH:26]C(OC(C)(C)C)=O)=[O:22])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:34][C:35](=[O:40])[O:36][CH:37]([CH3:39])[CH3:38])[CH2:6][C@@H:5]1[CH3:41])(=[O:3])[CH3:2].[ClH:42]>O1CCOCC1>[ClH:42].[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:15]=[CH:16][C:17]([CH2:20][C:21]([NH:23][CH2:24][CH2:25][NH2:26])=[O:22])=[CH:18][CH:19]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:34][C:35](=[O:40])[O:36][CH:37]([CH3:38])[CH3:39])[CH2:6][C@@H:5]1[CH3:41])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 867094181-methylethyl {(2S,4R)-1-acetyl-6-[4-(2-{[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]amino}-2-oxoethyl)phenyl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate

Product 1

HCID 714685031-methylethyl [(2S,4R)-1-acetyl-6-(4-{2-[(2-aminoethyl)amino]-2-oxoethyl}phenyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate hydrochlorideYield 52.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 1-methylethyl {(2S,4R)-1-acetyl-6-[4-(2-{[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]amino}-2-oxoethyl)phenyl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate (for a preparation see Intermediate 38) (60 mg, 0.106 mmol) in 1,4-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 residue was triturated with Et2O and the solid isolated by filtration to give 1-methylethyl [(2S,4R)-1-acetyl-6-(4-{2-[(2-aminoethyl)amino]-2-oxoethyl}phenyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate hydrochloride (28 mg, 0.056 mmol, 52.6% yield) as a pale yellow solid. LCMS (HpH, 2 min), Rt=0.79 min, MH+=467.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was triturated with Et2O
  3. customthe solid isolated by filtration

Sources & evidence

ORD record
ord-43c22f94392847cea12d1cc6de76bb08
Source dataset
uspto-grants-2015_03
Patent number
US08993554B2

Reaction notes

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