2-Propanol, reaction products with ammonia, distn. residues → HCID 57470874, compound

HRID 2265716Notes

Reaction equation

HRID 2265716 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:14]([F:15])=[CH:13][C:12]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:11]([F:27])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH3:28].C(O)(C)C>>[NH2:28][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:14]([F:15])=[CH:13][C:12]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:11]([F:27])[CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 183319422-Propanol, reaction products with ammonia, distn. residuesHCID 57470873Phenylmethyl N-[4-[(6-chloro-4-pyrimidinyl)oxy]-2,5-difluorophenyl]carbamate

Product 1

HCID 57470874HCID 57470874, compoundYield 15%

Conditions

Temperature
120 °C

Procedure

A mixture of benzyl [4-(4-chloropyrimidin-6-yloxy)-2,5-difluorophenyl]carbamate (3.92 g) and 2M ammonia-isopropanol (50 ml) was heated at 120° C. for 2 days in a sealed tube. The reaction mixture was allowed to cool to room temperature, then concentrated under reduced pressure. The resultant residue was partitioned between ethyl acetate and a 10% aqueous solution of potassium bisulfate. The organic layer was washed with brine, dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure and the resultant residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent; heptane:ethyl acetate=1:2). Fractions containing the target compound were concentrated under reduced pressure and the residue was dried under reduced pressure to provide the titled compound as pale yellow crystals (561 mg, 15%).

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe resultant residue was partitioned between ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe solvent was concentrated under reduced pressure
  7. customthe resultant residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent; heptane:ethyl acetate=1:2)
  8. additionFractions containing the target compound
  9. concentrationwere concentrated under reduced pressure
  10. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-e676fada427444b695b04235d1a80c14
Source dataset
uspto-grants-2010_12
Patent number
US07855290B2

Reaction notes

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