Water → HCID 86732557, compound

HRID 711410Notes

Reaction equation

HRID 711410 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[N:9]2[CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)[CH:12]=[C:8]2[C:7](=[O:20])[NH:6][CH2:5]1.[S:21](Cl)([CH3:24])(=[O:23])=[O:22].O>C(Cl)Cl>[CH3:24][S:21]([O:1][CH2:2][CH2:3][CH:4]1[N:9]2[CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)[CH:12]=[C:8]2[C:7](=[O:20])[NH:6][CH2:5]1)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 86732558HCID 86732558, compound

Product 1

HCID 86732557HCID 86732557, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(2-hydroxyethyl)-7-(3-chlorophenyl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one (128 mg, 0.44 mmol) in DCM (10 ml), mesyl chloride (58 ul, 0.748 mmol) and TEA (200 ul, 1.48 mmol), were added. The resulting solution was stirred at room temperature, after 1 h the reaction mixture was portioned between DCM and water. The organic layers were washed with brine, dried over Na2SO4 and concentrated. The crude was triturated with diethyl ether and filtered to give 2-[1-oxo-7-(3-chlorophenyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]ethyl methanesulfonate as a solid 157 mg (97%).

Workup

  1. washThe organic layers were washed with brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude was triturated with diethyl ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-4fa779cb2ebe4cbf89685aaf43b43095
Source dataset
uspto-grants-2015_11
Patent number
US09181258B2

Reaction notes

Loading…