Water → HCID 118051797, compound

HRID 595864Notes

Reaction equation

HRID 595864 reaction equation
[Br:1][C:2]1[C:3]([NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[N:4][CH:5]=[C:6]([C@@H:8]2[CH2:13][CH2:12][CH2:11][C@H:10]([O:14][Si](C(C)(C)C)(C)C)[CH2:9]2)[N:7]=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31].O>C(Cl)Cl>[CH3:29][S:30]([O:14][C@H:10]1[CH2:11][CH2:12][CH2:13][C@@H:8]([C:6]2[CH:5]=[N:4][C:3]([NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[C:2]([Br:1])[N:7]=2)[CH2:9]1)(=[O:32])=[O:31]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chloride2×HCID 131734600HCID 131734600, compound

Product 1

HCID 118051797HCID 118051797, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (+/−)-N-(3-bromo-5-((1R,35)-3-((tert-butyldimethylsilyl)oxy)cyclohexyl)pyrazin-2-yl)pivalamide (72 mg, 0.202 mmol) in CH2Cl2 (2021 μL) at 0° C. was added TEA (56.3 μL, 0.404 mmol) and methanesulfonyl chloride (18.90 μL, 0.243 mmol). The resulting mixture was stirred at room temperature for 3h. Another TEA (56.3 μL, 0.404 mmol) and Methanesulfonyl chloride (18.90 μL, 0.243 mmol) was added, and stirred for 6h. Worked up the reaction by adding water. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified with flash chromatography eluting with 0-100% EtOAc/heptane to provide 54 mg of (+/−)-(1S,3R)-3-(6-bromo-5-pivalamidopyrazin-2-yl)cyclohexyl methanesulfonate in 61.5% yield. LCMS (m/z): 436.1 (MH+), 0.75 min.

Workup

  1. stirringstirred for 6h
  2. customthe reaction
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified with flash chromatography
  8. washeluting with 0-100% EtOAc/heptane

Sources & evidence

ORD record
ord-c027ac9fc70f4b31bb7877c15931b090
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

Loading…