Water → HCID 58119369, compound

HRID 2167494Notes

Reaction equation

HRID 2167494 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[N:12]=2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH:13]3[CH2:18][CH2:17][N:16]([S:29]([CH3:28])(=[O:31])=[O:30])[CH2:15][CH2:14]3)[N:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58119379HCID 58119379, compound

Product 1

HCID 58119369HCID 58119369, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-[2-(4-fluorophenyl)-1,3-oxazol-4-yl]piperidine (220 mg, 0.90 mmol) in DCM (20 mL) was treated with DIEA (0.31 mL, 1.8 mmol) and allowed to stir at rt for 15 min. Methanesulfonyl chloride (0.2 mL, 2.7 mmol) was slowly added to the solution and the resulting mixture was stirred at rt for 2 hr. Upon completion of the reaction, DCM (20 mL) and water (40 mL) was added to the mixture and the two layers were partitioned. The organic layer was dried with MgSO4, filtered and concentrated. The residue was purified by reverse phase HPLC to afford the title compound (100 mg). LC/MS: m/e 325.2 (M+H)+.

Workup

  1. stirringthe resulting mixture was stirred at rt for 2 hr
  2. additionwas added to the mixture
  3. customthe two layers were partitioned
  4. dry with materialThe organic layer was dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-0042355b016a43a6b581c714a0ea8e99
Source dataset
uspto-grants-2015_06
Patent number
US09045467B2

Reaction notes

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