Hydrochloric Acid → HCID 89544881, compound

HRID 2283446Notes

Reaction equation

HRID 2283446 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:11][C:12]([CH:14]2[CH2:19][CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15]2)=[O:13])[CH2:9][CH3:10])=[C:4]([F:27])[C:3]=1[C:28]([C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1)=[O:29].Cl.O1CCOCC1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:11][C:12]([CH:14]2[CH2:19][CH2:18][CH2:17][NH:16][CH2:15]2)=[O:13])[CH2:9][CH3:10])=[C:4]([F:27])[C:3]=1[C:28]([C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1)=[O:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 89544709HCID 89544709, compound

Product 1

HCID 89544881HCID 89544881, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-{[(1S)-1-{4-chloro-2-fluoro-3-[(pyridin-3-yl)carbonyl]phenyl}-propyl]carbamoyl}piperidine-1-carboxylate (220 mg, 0.44 mmol) in DCM (3 mL) was added 4M HCl in dioxane (0.44 mL, 1.75 mmol, 4 eq) and the reaction stirred for 18 h. The mixture was concentrated and then triturated with diethyl ether (˜5 mL) and the pale green solid filtered off and dried in a vacuum oven to give N-[(1S)-1-{4-chloro-2-fluoro-3-[(pyridin-3-yl)carbonyl]phenyl}propyl]piperidine-3-carboxamide as a white solid (80.0 mg).

Workup

  1. concentrationThe mixture was concentrated
  2. customtriturated with diethyl ether (˜5 mL)
  3. filtrationthe pale green solid filtered off
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-890e35b762674acb8ed276ac9c4edc84
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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