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

HRID 2366940Notes

Reaction equation

HRID 2366940 reaction equation
[ClH:1].[CH3:2][CH:3]([O:5][C:6](=[O:37])[NH:7][C@H:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]3[N:19]=[N:20][N:21]([CH2:23][CH2:24][NH:25]C(OC(C)(C)C)=O)[CH:22]=3)[CH:16]=2)[N:11]([C:33](=[O:35])[CH3:34])[C@@H:10]([CH3:36])[CH2:9]1)[CH3:4].CCOCC>O1CCOCC1>[ClH:1].[C:33]([N:11]1[C:12]2[C:17](=[CH:16][C:15]([C:18]3[N:19]=[N:20][N:21]([CH2:23][CH2:24][NH2:25])[CH:22]=3)=[CH:14][CH:13]=2)[C@H:8]([NH:7][C:6](=[O:37])[O:5][CH:3]([CH3:2])[CH3:4])[CH2:9][C@@H:10]1[CH3:36])(=[O:35])[CH3:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 681854041-methylethyl ((2S,4R)-1-acetyl-6-{1-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-1H-1,2,3-triazol-4-yl}-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate

Product 1

HCID 529340991-methylethyl {(2S,4R)-1-acetyl-6-[1-(2-aminoethyl)-1H-1,2,3-triazol-4-yl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate hydrochlorideYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

HCl (4M in 1,4-dioxane, 2 mL, 8 mmol) was added to a solution of 1-methylethyl((2S,4R)-1-acetyl-6-{1-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-1H-1,2,3-triazol-4-yl}-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate (for a preparation, see intermediate 77) (108 mg, 0.22 mmol) in 1,4-dioxane (0.5 mL). The mixture was stirred at room temperature for 16 h. Et2O (5 mL) was added and the mixture stirred for 1 h. The solid formed was filtered off, washed with Et2O and dried under house vacuum to give 1-methylethyl {(2S,4R)-1-acetyl-6-[1-(2-aminoethyl)-1H-1,2,3-triazol-4-yl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate hydrochloride (75 mg, 0.172 mmol, 80%) as a colourless solid. LCMS (method G): Retention time 0.55 min, [M+H]+=401.1

Workup

  1. customfor a preparation
  2. stirringthe mixture stirred for 1 h
  3. customThe solid formed
  4. filtrationwas filtered off
  5. washwashed with Et2O
  6. customdried under house vacuum

Sources & evidence

ORD record
ord-7f9fd22d45494822a637a38decc1ac27
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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