Methanesulfonyl chloride → HCID 67070003, compound

HRID 2390807Notes

Reaction equation

HRID 2390807 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:13]=[C:12]([C:20]3[C:21]([O:26][CH3:27])=[N:22][CH:23]=[CH:24][CH:25]=3)[C:11]=2[OH:28])=[CH:4][CH:3]=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>N1C=CC=CC=1.CCOC(C)=O>[C:16]([C:14]1[CH:13]=[C:12]([C:20]2[C:21]([O:26][CH3:27])=[N:22][CH:23]=[CH:24][CH:25]=2)[C:11]([OH:28])=[C:10]([CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([NH:1][S:30]([CH3:29])(=[O:32])=[O:31])=[CH:3][CH:4]=2)[CH:15]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 67070050HCID 67070050, compound

Product 1

HCID 67070003HCID 67070003, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

step 5—To a solution of 54 (156 mg, 0.415 mmol) in pyridine (5 mL) at 0° C. was added methanesulfonyl chloride (0.050 mL, 0.643 mmol). The reaction was gradually warmed to RT and stirred for 1.5 h then diluted with EtOAc. The organic layer was washed sequentially with saturated aqueous CuSO4, brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (10 to 50% EtOAc) to afford 115 mg (61%) of N-(4-{2-[5-tert-butyl-2-hydroxy-3-(2-methoxy-pyridin-3-yl)-phenyl]-ethyl}-phenyl)-methanesulfonamide (56) as a colorless oil.

Workup

  1. washThe organic layer was washed sequentially with saturated aqueous CuSO4, brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by SiO2 chromatography
  6. washeluting with an EtOAc/hexane gradient (10 to 50% EtOAc)

Sources & evidence

ORD record
ord-9df3cc3447a24d7fa81d3570e1c87a46
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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