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

HRID 2366945Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2366945
[CH3:1][CH:2]([O:4][C:5](=[O:36])[NH:6][C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[N:18]=[CH:19][N:20]([CH2:22][CH2:23][NH:24]C(OC(C)(C)C)=O)[CH:21]=3)[CH:15]=2)[N:10]([C:32](=[O:34])[CH3:33])[C@@H:9]([CH3:35])[CH2:8]1)[CH3:3].[ClH:37].CCOCC>O1CCOCC1>[ClH:37].[C:32]([N:10]1[C:11]2[C:16](=[CH:15][C:14]([C:17]3[N:18]=[CH:19][N:20]([CH2:22][CH2:23][NH2:24])[CH:21]=3)=[CH:13][CH:12]=2)[C@H:7]([NH:6][C:5](=[O:36])[O:4][CH:2]([CH3:1])[CH3:3])[CH2:8][C@@H:9]1[CH3:35])(=[O:34])[CH3:33]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 681854051-methylethyl ((2S,4R)-1-acetyl-6-{1-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-1H-imidazol-4-yl}-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate

Produkt 1

HCID 529343311-methylethyl {(2S,4R)-1-acetyl-6-[1-(2-aminoethyl)-1H-imidazol-4-yl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate hydrochlorideAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 1-methylethyl((2S,4R)-1-acetyl-6-{1-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-1H-imidazol-4-yl}-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate (for a preparation, see Intermediate 79) (47 mg, 0.094 mmol) in 1,4-dioxane (0.5 mL) was treated with HCl (4M in 1,4-dioxane, 2 mL, 8 mmol) and the resulting mixture was stirred at room temperature for 4 h. Et2O (10 mL) was added and the resulting mixture stirred for 15 min. 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-imidazol-4-yl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate hydrochloride (25 mg, 0.057 mmol, 61%) as a brown solid.

Aufarbeitung

  1. stirringthe resulting mixture stirred for 15 min
  2. customThe solid formed
  3. filtrationwas filtered off
  4. washwashed with Et2O
  5. customdried under house vacuum

Quellen und Nachweise

ORD-Eintrag
ord-9c4d7d3e5c7c4dad93c4e5a2e416697d
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697725B2

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