Diisopropylethylamine → HCID 131722998, compound

HRID 429881Notes

Reaction equation

HRID 429881 reaction equation
C1(N)C([F:7])=C(F)C(F)=C(N)C=1F.Cl.Cl.C(O[C:20]([NH:22][CH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][CH:29]([C:32]2[CH:39]=[C:38](F)[CH:37]=[CH:36][C:33]=2C#N)[CH2:28][CH2:27]1)=[O:21])(C)(C)C.[N+](C1C=CC(OC([N:53]2[C@@H:57]([C:58]3[CH:63]=[CH:62][C:61]([F:64])=[C:60]([F:65])[CH:59]=3)[C@@H:56]([CH2:66][N:67]3[CH:71]=[CH:70][N:69]=[CH:68]3)[O:55][C:54]2=[O:72])=O)=CC=1)([O-])=O.C(N(CC)C(C)C)(C)C>>[F:7][C:37]1[CH:36]=[CH:33][C:32]([CH:29]2[CH2:28][CH2:27][N:26]([CH2:25][CH2:24][CH2:23][NH:22][C:20]([N:53]3[C@@H:57]([C:58]4[CH:63]=[CH:62][C:61]([F:64])=[C:60]([F:65])[CH:59]=4)[C@@H:56]([CH2:66][N:67]4[CH:71]=[CH:70][N:69]=[CH:68]4)[O:55][C:54]3=[O:72])=[O:21])[CH2:31][CH2:30]2)=[CH:39][CH:38]=1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 18353389HCID 18353389, compoundHCID 57143409HCID 57143409, compound

Product 1

HCID 131722998HCID 131722998, compound

Procedure

To a suspension of the dihydrochloride salt of 3-[4-(4-fluorophenyl)piperidin-1-yl]propylamine (77 mg, 0.25 mmol) (see Example 1) and (4S, 5R) 4-(3,4-difluorophenyl)-5-(imidazol-1-ylmethyl)-2-oxo-oxazolidine-3-carboxylic acid (4-nitrophenyl) ester (112 mg, 0.25 mmol) in dry, degassed N,N-dimethylformamide (1 mL) was added N,N-diisopropylethylamine (88 μL, 0.50 mmol). The reaction mixture was stirred at ambient temperature for 20 h when the volatiles were removed under reduced pressure. The residue was dissolved in ethyl acetate (50 mL) and washed with 10% aqueous sodium carbonate solution (6×50 mL), brine (1×50 mL), dried over magnesium sulfate and filtered. The volatiles were removed under reduced pressure to give a foam. The hydrochloride salt was prepared according to standard procedures to afford (4S, 5R)-4-(3,4-difluorophenyl)-5-imidazol-1-ylmethyl-2-oxo-oxazolidine-3-carboxylic acid{3-[4-(4-fluorophenyl)piperidin-1-yl]propyl}amide as a solid.

Workup

  1. customin dry
  2. customdegassed N,N-dimethylformamide (1 mL)
  3. customwere removed under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
  5. washwashed with 10% aqueous sodium carbonate solution (6×50 mL), brine (1×50 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customThe volatiles were removed under reduced pressure
  9. customto give a foam

Sources & evidence

ORD record
ord-b4d59ea931ac46eb83dc43622f05f43b
Source dataset
uspto-grants-2001_11
Patent number
US06319932B1

Reaction notes

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