HCID 89544689, compound → HCID 89545056, compound

HRID 2283400Notes

Reaction equation

HRID 2283400 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:11]C(=O)OC(C)(C)C)[CH2:9][CH3:10])=[C:4]([F:19])[C:3]=1[C:20]([C:22]1[CH:23]=[N:24][C:25]([O:28]C)=[CH:26][CH:27]=1)=[O:21]>Cl.O>[NH2:11][C@@H:8]([C:5]1[C:4]([F:19])=[C:3]([C:20]([C:22]2[CH:27]=[CH:26][C:25](=[O:28])[NH:24][CH:23]=2)=[O:21])[C:2]([Cl:1])=[CH:7][CH:6]=1)[CH2:9][CH3:10]

Participants

4

Reactant 1

HCID 89544689HCID 89544689, compound

Product 1

HCID 89545056HCID 89545056, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

Step 2 Tert-butyl N-[(1R)-1-{4-chloro-2-fluoro-3-[(6-methoxypyridin-3-yl)carbonyl]phenyl}-propyl]carbamate (90.0 mg, 0.21 mmol) was dissolved in 6M HCl in water (5.0 mL) and the reaction was heated at reflux for 8 h. Complete conversion. Mixture was quenched with NaOH (5M) until pH˜5, then extracted with 4:1 CHCl3:IPA (3×20 mL). Combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to give 5-({3-[(1R)-1-aminopropyl]-6-chloro-2-fluorophenyl}carbonyl)-1,2-dihydropyridin-2-one (56.2 mg, 88% yield).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 8 h
  3. customMixture was quenched with NaOH (5M) until pH˜5
  4. extractionextracted with 4:1 CHCl3
  5. dry with materialCombined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-caeb35e8f3804cf7a9f6a99da7fe4297
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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