HCID 67358696, compound → HCID 87377264, compound

HRID 245510Notes

Reaction equation

HRID 245510 reaction equation
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[C:23]([CH2:24][OH:25])=[CH:22][C:12]3[C:13]([C:16]4[N:17]=[C:18]([CH3:21])[O:19][CH:20]=4)=[N:14][O:15][C:11]=3[C:10]=2[F:26])[CH2:3]1>C(Cl)Cl.O=[Mn]=O>[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[C:23]([CH:24]=[O:25])=[CH:22][C:12]3[C:13]([C:16]4[N:17]=[C:18]([CH3:21])[O:19][CH:20]=4)=[N:14][O:15][C:11]=3[C:10]=2[F:26])[CH2:3]1

Participants

4

Reactant 1

HCID 67358696HCID 67358696, compound

Product 1

HCID 87377264HCID 87377264, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

MnO2 (227 mg, 2.8 mmol) was added at 0° C. to a solution of {6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-3-(2-methyl-1,3-oxazol-4-yl)-1,2-benzoxazol-5-yl}methanol Intermediate 311, 50 mg, 0.13 mmol) in anhydrous DCM (5 mL), and the mixture was allowed to stir for 1 h at room temperature. The reaction mixture was filtered and the solvents were removed under vacuum and the residue was purified by silica gel chromatography using ethyl acetate-pet. ether gradient to give product as a solid. Yield: 37 mg, (75%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvents were removed under vacuum
  3. customthe residue was purified by silica gel chromatography
  4. customto give product as a solid

Sources & evidence

ORD record
ord-b698c6a74a8e4ba2b03f126544ca42c0
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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