Hydrochloric Acid → HCID 86669273, compound

HRID 2366939Notes

Reaction equation

HRID 2366939 reaction equation
[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:21]=[C:20]([CH2:22][CH2:23][NH:24]C(OC(C)(C)C)=O)[O:19][N:18]=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:21]=[C:20]([CH2:22][CH2:23][NH2:24])[O:19][N:18]=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]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 68185403HCID 68185403, compound

Product 1

HCID 86669273HCID 86669273, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-methylethyl((2S,4R)-1-acetyl-6-{5-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-1,2,4-oxadiazol-3-yl}-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate (for a preparation, see Intermediate 76) (260 mg, 0.518 mmol) in 1,4-Dioxane (1 mL) was treated with HCl (4N in 1,4-dioxane, 1.00 mL, 4 mmol) and the resulting mixture was stirred at room temperature for 16 h. Et2O (10 mL) was then added and the precipitate formed was triturated then filtered off to give 1-methylethyl {(2S,4R)-1-acetyl-6-[5-(2-aminoethyl)-1,2,4-oxadiazol-3-yl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate hydrochloride (195 mg, 0.446 mmol, 86%) as an off white solid.

Workup

  1. customthe precipitate formed
  2. customwas triturated
  3. filtrationthen filtered off

Sources & evidence

ORD record
ord-f602aefcc96f4b048ae8f1affd43fea7
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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