1,1-Dimethylethyl [(4r)-4-(5-chloro-2-cyano-4-fluorophenoxy)-4-(1-methyl-1h-imidazol-2-yl)butyl]-carbamate → 2-[[(1r)-4-Amino-1-(1-methyl-1h-imidazol-2-yl)butyl]oxy]-4-chloro-5-fluoro-benzonitrile hydrochloride

HRID 352133Notes

Reaction equation

HRID 352133 reaction equation
[Cl:1][C:2]1[C:3]([F:29])=[CH:4][C:5]([C:27]#[N:28])=[C:6]([CH:26]=1)[O:7][C@@H:8]([C:20]1[N:21]([CH3:25])[CH:22]=[CH:23][N:24]=1)[CH2:9][CH2:10][CH2:11][NH:12]C(=O)OC(C)(C)C>Cl.O1CCOCC1>[ClH:1].[NH2:12][CH2:11][CH2:10][CH2:9][C@@H:8]([O:7][C:6]1[CH:26]=[C:2]([Cl:1])[C:3]([F:29])=[CH:4][C:5]=1[C:27]#[N:28])[C:20]1[N:21]([CH3:25])[CH:22]=[CH:23][N:24]=1

Participants

4

Reactant 1

HCID 914130451,1-Dimethylethyl [(4r)-4-(5-chloro-2-cyano-4-fluorophenoxy)-4-(1-methyl-1h-imidazol-2-yl)butyl]-carbamate

Product 1

HCID 698293472-[[(1r)-4-Amino-1-(1-methyl-1h-imidazol-2-yl)butyl]oxy]-4-chloro-5-fluoro-benzonitrile hydrochlorideYield 157%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

The product of step (c) (0.33 g, 0.78 mmol) was dissolved in 4M hydrochloric acid in dioxan (10 ml) and stirred for 10 minutes. The solvent was removed in vacuo and the solid residue triturated with ethyl acetate. The white solid was filtered off and dried under high vacuum to give the title compound (0.22 g, 70%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe solid residue triturated with ethyl acetate
  3. filtrationThe white solid was filtered off
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-0baef9a194c84897ad0469f4d9577267
Source dataset
uspto-grants-2004_06
Patent number
US06743939B2

Reaction notes

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