Hydrochloric Acid → HCID 52933865, compound

HRID 2366933Notes

Reaction equation

[CH3:1][CH:2]([O:4][C:5](=[O:35])[NH:6][C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[O:21][N:20]=[C:19]([CH2:22][NH:23]C(OC(C)(C)C)=O)[N:18]=3)[CH:15]=2)[N:10]([C:31](=[O:33])[CH3:32])[C@@H:9]([CH3:34])[CH2:8]1)[CH3:3].[ClH:36]>O1CCOCC1>[ClH:36].[C:31]([N:10]1[C:11]2[C:16](=[CH:15][C:14]([C:17]3[O:21][N:20]=[C:19]([CH2:22][NH2:23])[N:18]=3)=[CH:13][CH:12]=2)[C@H:7]([NH:6][C:5](=[O:35])[O:4][CH:2]([CH3:1])[CH3:3])[CH2:8][C@@H:9]1[CH3:34])(=[O:33])[CH3:32]

Participants

Conditions

Temperature: 4 °C

Procedure

To a solution of 1-methylethyl((2S,4R)-1-acetyl-6-{3-[({[(1,1-dimethylethyl)oxy]carbonyl}amino)methyl]-1,2,4-oxadiazol-5-yl}-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate (for a preparation, see Intermediate 62) (100 mg, 0.205 mmol) in 1,4-dioxane (0.5 mL) at room temperature was added HCl (4N in 1,4-dioxane, 2 mL, 8 mmol) and the resulting mixture was stirred at this temperature for 3 h than at 4° C. for 16 h before being warmed to room temperature. The residue was triturated with Et2O then purified using MDAP (modifier: ammonium bicarbonate). The residue obtained was dissolved in 1,4-dioxane (2 mL) and treated with HCl (4N in dioxane, 1 mL). The resulting mixture was concentrated in vacuo and the residue triturated with Et2O to give 1-methylethyl {(2S,4R)-1-acetyl-6-[3-(aminomethyl)-1,2,4-oxadiazol-5-yl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate hydrochloride (9 mg, 0.021 mmol, 10.35% yield).

Workup

customat room temperature
temperaturebefore being warmed to room temperature
customThe residue was triturated with Et2O
customthen purified
customThe residue obtained
concentrationThe resulting mixture was concentrated in vacuo
customthe residue triturated with Et2O

Sources & evidence

ORD record: ord-aa6dc63f43874fc593e8d2ca89221cbd
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697725B2

Reaction notes

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