Methanesulfonyl chloride → HCID 44247759, compound

HRID 2088358Notes

Reaction equation

HRID 2088358 reaction equation
CS(Cl)(=O)=O.[CH:6]1([C:12]2[O:13][C:14]3[CH:20]=[C:19]([C:21]([N:23]4[CH2:26][CH:25](O)[CH2:24]4)=[O:22])[CH:18]=[CH:17][C:15]=3[N:16]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.CCN(C(C)C)C(C)C.[N:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[N:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1>C(Cl)Cl.CN(C=O)C>[CH:6]1([C:12]2[O:13][C:14]3[CH:20]=[C:19]([C:21]([N:23]4[CH2:26][CH:25]([N:46]5[CH2:47][CH2:48][N:43]([C:38]6[CH:39]=[CH:40][CH:41]=[CH:42][N:37]=6)[CH2:44][CH2:45]5)[CH2:24]4)=[O:22])[CH:18]=[CH:17][C:15]=3[N:16]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531Diisopropylethylamine2×HCID 944591-(2-Pyridyl)piperazineHCID 66769667HCID 66769667, compound

Product 1

HCID 44247759HCID 44247759, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.152 mL, 1.9 mmol) was added dropwise to a solution of (2-cyclohexyl-benzooxazol-6-yl)-(3-hydroxy-azetidin-1-yl)-methanone (0.48 g, 1.6 mmol) and DIPEA (0.558 mL, 3.2 mmol) in DCM (20 mL) at −40° C. under nitrogen Immediately following the addition, the cooling bath was removed and the mixture slowly warmed to room temperature. The resulting mixture was then washed with water, dried using magnesium sulfate, filtered, and the solvent removed under reduced pressure. The resulting residue was dissolved in acetonitrile (1 mL). DIPEA (0.41 mL, 2.4 mmol) and N-(2-pyridyl)piperazine (1.6 mmol) were added. The resulting mixture was then microwaved at 160° C. for 4 hours. DMF (3 mL) was added to the resulting mixture, which was then purified by reverse phase liquid chromatography. The fractions containing product were diluted with 1N HCl (5 mL) and then lyophilized to yield 2-cyclohexyl-6-{[3-(4-pyridin-2-ylpiperazin-1-yl)azetidin-1-yl]carbonyl}-1,3-benzoxazole as its corresponding hydrochloride salt.

Workup

  1. additionthe addition
  2. customthe cooling bath was removed
  3. washThe resulting mixture was then washed with water
  4. customdried
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. dissolutionThe resulting residue was dissolved in acetonitrile (1 mL)
  8. customThe resulting mixture was then microwaved at 160° C. for 4 hours
  9. customwas then purified by reverse phase liquid chromatography
  10. additionThe fractions containing product
  11. additionwere diluted with 1N HCl (5 mL)

Sources & evidence

ORD record
ord-a6d10fbc754a47269d2426a329577c49
Source dataset
uspto-grants-2013_05
Patent number
US08435977B2

Reaction notes

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