Methanesulfonyl chloride → HCID 118046413, compound

HRID 595808Notes

Reaction equation

HRID 595808 reaction equation
[Br:1][C:2]1[C:3]([NH2:14])=[N:4][CH:5]=[C:6]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[N:7]=1.CCN(C(C)C)C(C)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl>[Br:1][C:2]1[C:3]([NH2:14])=[N:4][CH:5]=[C:6]([CH:8]2[CH2:9][CH2:10][N:11]([S:25]([CH3:24])(=[O:27])=[O:26])[CH2:12][CH2:13]2)[N:7]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 118045729HCID 118045729, compound

Product 1

HCID 118046413HCID 118046413, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-bromo-5-(piperidin-4-yl)pyrazin-2-amine (50 mg, 0.194 mmol) in DCM (2 mL) in ice bath was added DIEA (340 μl, 1.945 mmol) and methanesulfonyl chloride (16.67 μl, 0.214 mmol). The reaction mixture was stirred for 60 min. The reaction mixture was extracted with DCM. The organic layer was washed with brine, dried over sodium sulfate, filtered and evaporated in vacuo. (30 mg, 46%). LCMS (m/z): 335.2/337.2 (MH+), 0.572 min.

Workup

  1. extractionThe reaction mixture was extracted with DCM
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. custom335.2/337.2 (MH+), 0.572 min.

Sources & evidence

ORD record
ord-4b113f1b6ab14bb2a92067a4dee05d3a
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

Loading…