Hydrochloric Acid → HCID 89544904, compound

HRID 2283410Notes

Reaction equation

HRID 2283410 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](=[O:29])[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([C:27]#[N:28])[CH:20]=2)[C:12]=1[F:30])[CH2:9][CH3:10])(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[NH2:7][C@@H:8]([C:11]1[C:12]([F:30])=[C:13]([C:14]([Cl:17])=[CH:15][CH:16]=1)[C:18]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([CH:20]=1)[C:27]#[N:28])=[O:29])[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 89544970HCID 89544970, compound

Product 1

HCID 89544904HCID 89544904, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step 5 To a solution of {(R)-1-[4-Chloro-3-(3-cyano-4-methoxy-benzoyl)-2-fluoro-phenyl]-propyl}-carbamic acid tert-butyl ester (59 mg, 0.13 mmol) in DCM (2 mL) was added 4M HCl in dioxane (0.17 mL, 0.66 mmol, 5 eq.) and the reaction mixture was stirred for 60 hours. The mixture was partitioned between DCM (10 mL) and water (10 mL) made basic with 5M NaOH. The aqueous phase was extracted with further DCM (10 mL) and then the combined organics were dried (MgSO4), filtered and concentrated to give 5-[3-((R)-1-amino-propyl)-6-chloro-2-fluoro-benzoyl]-2-methoxy-benzonitrile (41 mg, 0.12 mmol) as a viscous gum.

Workup

  1. customThe mixture was partitioned between DCM (10 mL) and water (10 mL)
  2. extractionThe aqueous phase was extracted with further DCM (10 mL)
  3. dry with materialthe combined organics were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a9ee40f7e82a4f53ae1337e46a3f330d
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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