Methanesulfonyl chloride → HCID 71523273, compound

HRID 711417Notes

Reaction equation

HRID 711417 reaction equation
Cl.[F:2][C:3]([F:22])([F:21])[O:4][C:5]1[CH:6]=[C:7]([C:11]2[CH:12]=[C:13]3[C:18](=[O:19])[NH:17][CH2:16][CH2:15][N:14]3[CH:20]=2)[CH:8]=[CH:9][CH:10]=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25].CCN([CH:34]([CH3:36])[CH3:35])C(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.C(OCC)(=O)C>[O:19]=[C:18]1[NH:17][CH2:16][C@H:15]([CH2:12][CH2:13][NH:14][S:24]([CH3:23])(=[O:26])=[O:25])[N:14]2[C:20]([C:35]3[CH:34]=[CH:36][CH:6]=[CH:5][CH:10]=3)=[C:11]([C:7]3[CH:8]=[CH:9][CH:10]=[C:5]([O:4][C:3]([F:2])([F:21])[F:22])[CH:6]=3)[CH:12]=[C:13]12

Participants

7

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 86732566HCID 86732566, compound

Product 1

HCID 71523273HCID 71523273, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

40 mg (0.096 mmol) of 1(4S)-4-(2-aminoethyl)-6-phenyl)-7-[3-(trifluoromethoxy)phenyl]-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one hydrochloride were dissolved in 3 ml of DCM. To the obtained solution, 15 μl (0.192 mmol) of methanesulfonyl chloride, 57 μl (0.33 mmol) of DIPEA, were added. The mixture was stirred at rt for 2 hours, the solution was portioned between ethyl acetate and saturated aqueous solution of NaHCO3, the organic layer was washed with brine, dried over Na2SO4 and evaporated under vacuum. The product was purified by HPLC preparative method 2 and isolated as a off-white solid 24 mg (51%) as a white solid.

Workup

  1. washthe organic layer was washed with brine
  2. dry with materialdried over Na2SO4
  3. customevaporated under vacuum
  4. customThe product was purified by HPLC preparative method 2

Sources & evidence

ORD record
ord-7616578cf96540b68b1bcfb4efe51b08
Source dataset
uspto-grants-2015_11
Patent number
US09181258B2

Reaction notes

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