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

HRID 2366936Notes

Reaction equation

HRID 2366936 reaction equation
[CH3:1][CH:2]([O:4][C:5](=[O:37])[NH:6][C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[N:18]=[N:19][N:20]([CH2:22][CH2:23][CH2:24][NH:25]C(OC(C)(C)C)=O)[CH:21]=3)[CH:15]=2)[N:10]([C:33](=[O:35])[CH3:34])[C@@H:9]([CH3:36])[CH2:8]1)[CH3:3].[ClH:38]>O1CCOCC1>[ClH:38].[C:33]([N:10]1[C:11]2[C:16](=[CH:15][C:14]([C:17]3[N:18]=[N:19][N:20]([CH2:22][CH2:23][CH2:24][NH2:25])[CH:21]=3)=[CH:13][CH:12]=2)[C@H:7]([NH:6][C:5](=[O:37])[O:4][CH:2]([CH3:1])[CH3:3])[CH2:8][C@@H:9]1[CH3:36])(=[O:35])[CH3:34]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 681854011-methylethyl ((2S,4R)-1-acetyl-6-{1-[3-({[(1,1-dimethylethyl)oxy]carbonyl}amino)propyl]-1H-1,2,3-triazol-4-yl}-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate

Product 1

HCID 529338731-methylethyl {(2S,4R)-1-acetyl-6-[1-(3-aminopropyl)-1H-1,2,3-triazol-4-yl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate hydrochlorideYield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-methylethyl((2S,4R)-1-acetyl-6-{1-[3-({[(1,1-dimethylethyl)oxy]carbonyl}amino)propyl]-1H-1,2,3-triazol-4-yl}-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate (for a preparation, see Intermediate 73) (543 mg, 1.055 mmol) in 1,4-dioxane (1 mL) was treated with HCl (4N in 1,4-dioxane, 4.00 mL, 16 mmol) and the resulting mixture was stirred for 2 h at room temperature then concentrated in vacuo. The residue was co-evaporated twice with toluene then triturated with Et2O and filtered off to give 1-methylethyl {(2S,4R)-1-acetyl-6-[1-(3-aminopropyl)-1H-1,2,3-triazol-4-yl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate hydrochloride (370 mg, 0.771 mmol, 73% yield) as a brown solid.

Workup

  1. concentrationthen concentrated in vacuo
  2. customthen triturated with Et2O
  3. filtrationfiltered off

Sources & evidence

ORD record
ord-4a7f657d5adb4f40b018be24668cdfee
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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