Potassium Carbonate → HCID 66975908, compound

HRID 1022767Notes

Reaction equation

HRID 1022767 reaction equation
[NH2:1][CH2:2][C@H:3]1[C@H:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([F:17])[CH:11]=2)[O:8][CH2:7][CH2:6][N:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:4]1.Cl[C:26]1[N:31]=[CH:30][CH:29]=[CH:28][N:27]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([C@@H:9]2[O:8][CH2:7][CH2:6][N:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:4][C@H:3]2[CH2:2][NH:1][C:26]2[N:31]=[CH:30][CH:29]=[CH:28][N:27]=2)=[CH:11][C:12]=1[F:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 744042-ChloropyrimidineHCID 66975002tert-butyl (6R,7R)-6-(aminomethyl)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepane-4-carboxylate

Product 1

HCID 66975908HCID 66975908, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl (6R,7R)-6-(aminomethyl)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepane-4-carboxylate (120.7 mg), 2-chloropyrimidine (40.5 mg) and potassium carbonate (46.5 mg) in ethanol (3 mL) was stirred at room temperature overnight, and the solvent was evaporated under reduced pressure. The residue was partitioned between ethyl acetate and water, and the organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (97.8 mg).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0e5e0b2394784fb985e16c0def000fe4
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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