Hydrochloric Acid → HCID 89544538, compound

HRID 2283392Notes

Reaction equation

HRID 2283392 reaction equation
C(OC(=O)[NH:7][C@@H:8]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([C:18]([C:20]2[CH:21]=[N:22][C:23]([NH2:26])=[CH:24][CH:25]=2)=[O:19])[C:12]=1[F:27])[CH2:9][CH3:10])(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[NH2:7][C@@H:8]([C:11]1[C:12]([F:27])=[C:13]([C:18]([C:20]2[CH:21]=[N:22][C:23]([NH2:26])=[CH:24][CH:25]=2)=[O:19])[C:14]([Cl:17])=[CH:15][CH:16]=1)[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 89544725HCID 89544725, compound

Product 1

HCID 89544538HCID 89544538, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step 3 To a solution of {(R)-1-[3-(6-amino-pyridine-3-carbonyl)-4-chloro-2-fluoro-phenyl]-propyl}-carbamic acid tert-butyl ester (2.18 g, 4.43 mmol) in DCM (50 mL) was added 4M HCl in dioxane (7.75 mL, 31 mmol, 7 eq) and the reaction stirred for 18 h. Complete conversion. Mixture was concentrated and then triturated with diethyl ether (50 mL) and the solid filtered off and dried in a vacuum oven to give [3-((R)-1-amino-propyl)-6-chloro-2-fluoro-phenyl]-(6-amino-pyridin-3-yl)-methanone (1.54 g, 4.35 mmol, 98%) as a beige solid and the HCl salt

Workup

  1. concentrationMixture was concentrated
  2. customtriturated with diethyl ether (50 mL)
  3. filtrationthe solid filtered off
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-8b9c10953ec842bbb54c2a1c9f4c1b87
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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