Hydrochloric Acid → HCID 89544863, compound

HRID 2283412Notes

Reaction equation

HRID 2283412 reaction equation
C(OC(=O)[NH:7][C@@H:8]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19](=[O:28])[C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[C:22]([CH3:27])[CH:21]=2)[C:13]=1[F:29])[CH:9]1[CH2:11][CH2:10]1)(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[NH2:7][C@H:8]([CH:9]1[CH2:11][CH2:10]1)[C:12]1[C:13]([F:29])=[C:14]([C:19]([C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[C:22]([CH3:27])[CH:21]=2)=[O:28])[C:15]([Cl:18])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 89545318HCID 89545318, compound

Product 1

HCID 89544863HCID 89544863, compoundYield 102.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step 3 To a solution of {(R)-[3-(4-amino-3-methyl-benzoyl)-4-chloro-2-fluoro-phenyl]-cyclopropyl-methyl}-carbamic acid tert-butyl ester (570 mg, 1.32 mmol) in DCM (6 mL) was added 4M HCl in dioxane (1.65 mL, 6.58 mmol, 5 eq) and the reaction stirred for 18 hours. The resulting mixture was partitioned between DCM (50 mL) and water (20 mL) and basified with NaOH. Not all of the compound dissolved and so the aqueous phase was extracted with 4:1 CHCl3:IPA (2×30 mL). The combined organics were washed with brine (20 mL) and then dried (MgSO4), filtered and concentrated to give [3-((R)-amino-cyclopropyl-methyl)-6-chloro-2-fluoro-phenyl]-(4-amino-3-methyl-phenyl)-methanone (451 mg).

Workup

  1. customThe resulting mixture was partitioned between DCM (50 mL) and water (20 mL)
  2. dissolutionNot all of the compound dissolved and so the aqueous phase
  3. extractionwas extracted with 4:1 CHCl3
  4. washThe combined organics were washed with brine (20 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-92aaccd7fb104621b5683cd9c1a85931
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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