Hydrochloric Acid → HCID 52933867, compound

HRID 2366934Notes

Reaction equation

HRID 2366934 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[O:21][N:20]=[C:19]([CH2:22][CH2:23][NH:24]C(OC(C)(C)C)=O)[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]>O1CCOCC1>[ClH:37].[C:32]([N:10]1[C:11]2[C:16](=[CH:15][C:14]([C:17]3[O:21][N:20]=[C:19]([CH2:22][CH2:23][NH2:24])[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

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 68185398HCID 68185398, compound

Product 1

HCID 52933867HCID 52933867, compoundYield 11.45%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 1-methylethyl((2S,4R)-1-acetyl-6-{3-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-1,2,4-oxadiazol-5-yl}-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate (for a preparation, see Intermediate 66) (100 mg, 0.199 mmol) in 1,4-dioxane (0.5 mL) at room temperature was added HCl (4N in 1,4-dioxane, 2 mL, 8.00 mmol) and the resulting mixture was stirred at this temperature for 3 h then was left standing 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 1,4-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-(2-aminoethyl)-1,2,4-oxadiazol-5-yl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate hydrochloride (10 mg, 0.023 mmol, 11.45% yield) as a colourless solid.

Workup

  1. customat room temperature
  2. waitthen was left
  3. waitstanding at 4° C. for 16 h
  4. customThe residue was triturated with Et2O
  5. customthen purified
  6. customThe residue obtained
  7. concentrationThe resulting mixture was concentrated in vacuo
  8. customthe residue triturated with Et2O

Sources & evidence

ORD record
ord-fd830fcb080a4ef3ad6676e213684e0e
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

Loading…