Ammonium Chloride → HCID 86705193, compound

HRID 2401286Notes

Reaction equation

HRID 2401286 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:12][C@H:11]([CH:13]([CH3:15])[CH3:14])[N:10]([CH2:16][C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)=[O:18])[C:9]2=[O:30])=[CH:4][CH:3]=1.[CH2:31]([Mg]Br)[CH2:32][CH3:33].[Cl-].[NH4+]>C1COCC1.CN1C(=O)CCC1.C/C(/[O-])=C\C(C)=O.C/C(/[O-])=C\C(C)=O.C/C(/[O-])=C\C(C)=O.[Fe+3]>[O:30]=[C:9]1[N:8]([C:5]2[CH:6]=[N:7][C:2]([CH2:31][CH2:32][CH3:33])=[CH:3][CH:4]=2)[CH2:12][C@H:11]([CH:13]([CH3:15])[CH3:14])[N:10]1[CH2:16][C:17]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=1)=[O:18]

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 86705191HCID 86705191, compoundHCID 178455851HCID 178455851, compound

Product 1

HCID 86705193HCID 86705193, compound

Reagents, catalysts & solvents 3

HCID 53384555HCID 53384555, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a suspension of 2-[(5S)-3-(6-bromopyridin-3-yl)-2-oxo-5-(propan-2-yl)imidazolidin-1-yl]-N-[3-(trifluoromethyl)phenyl]acetamide (50 mg) and tris(2,4-pentanedionato)iron(III) (55 mg) in THF (1 mL) and NMP (0.1 mL) was added n-propylmagnesium bromide (2M solution in THF, 0.31 mL), and the mixture was stirred at room temperature for 1 hr. Saturated aqueous ammonium chloride solution was added thereto, the resulting mixture was extracted with acetic acid, and the organic layer was washed with water and brine. After drying over anhydrous sodium sulfate, the desiccant was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (hexane/ethyl acetate) to afford the title compound (24 mg).

Workup

  1. extractionthe resulting mixture was extracted with acetic acid
  2. washthe organic layer was washed with water and brine
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. filtrationthe desiccant was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-68a84c6d3c244c0ca6bf3e0f99a64dd5
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

Loading…