Hydrochloric Acid → HCID 117652816, compound

HRID 588399Notes

Reaction equation

HRID 588399 reaction equation
[CH2:1]([O:3][C:4]([O:6][CH:7]([N:9]1[C:13](=[O:14])[O:12][N:11]=[C:10]1[C:15]1[N:19]([CH3:20])[N:18]=[CH:17][C:16]=1[C:21]1[CH:49]=[CH:48][C:24]([C:25]([N:27]([C:41]2[C:46]([CH3:47])=[CH:45][CH:44]=[CH:43][N:42]=2)[C@@H:28]2[CH2:33][CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29]2)=[O:26])=[CH:23][CH:22]=1)[CH3:8])=[O:5])[CH3:2].Cl.O1CCOCC1>C(Cl)Cl>[C:4](=[O:5])([O:6][CH:7]([N:9]1[C:13](=[O:14])[O:12][N:11]=[C:10]1[C:15]1[N:19]([CH3:20])[N:18]=[CH:17][C:16]=1[C:21]1[CH:22]=[CH:23][C:24]([C:25](=[O:26])[N:27]([C:41]2[C:46]([CH3:47])=[CH:45][CH:44]=[CH:43][N:42]=2)[C@@H:28]2[CH2:33][CH2:32][CH2:31][NH:30][CH2:29]2)=[CH:48][CH:49]=1)[CH3:8])[O:3][CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 118898573HCID 118898573, compound

Product 1

HCID 117652816HCID 117652816, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl (3R)-3-[{4-[5-(4-{1-[(ethoxycarbonyl)oxy]ethyl}-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-1-methyl-1H-pyrazol-4-yl]benzoyl}(3-methylpyridin-2-yl)amino]piperidine-1-carboxylate (52 mg, 0.08 mmol) was dissolved in DCM (5 mL) and to the solution was added HCl in dioxane (0.5 mL, 4M solution, 2 mmol) and stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo. The resulting residue was triturated in diethyl ether to yield ethyl 1-{3-[1-methyl-4-(4-{(3-methylpyridin-2-yl)[(3R)-piperidin-3-yl]carbamoyl}phenyl)-1H-pyrazol-5-yl]-5-oxo-1,2,4-oxadiazol-4(5H)-yl}ethyl carbonate as a light yellow solid (40 mg, 80%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe resulting residue was triturated in diethyl ether

Sources & evidence

ORD record
ord-c936d4387376463daddeea3b796d9be1
Source dataset
uspto-grants-2016_01
Patent number
US09227956B2

Reaction notes

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