Methanesulfonyl chloride → 2-(7-Iodo-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl)ethyl methanesulfonate

HRID 711399Notes

Reaction equation

HRID 711399 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[OH:6][CH2:7][CH2:8][CH:9]1[N:14]2[CH:15]=[C:16]([I:18])[CH:17]=[C:13]2[C:12](=[O:19])[NH:11][CH2:10]1.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:4][S:1]([O:6][CH2:7][CH2:8][CH:9]1[N:14]2[CH:15]=[C:16]([I:18])[CH:17]=[C:13]2[C:12](=[O:19])[NH:11][CH2:10]1)(=[O:3])=[O:2]

Participants

6

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 867325494-(2-hydroxyethyl)-7-iodo-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one

Product 1

HCID 867325512-(7-Iodo-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl)ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Mesyl chloride (0.172 g, 1.50 mmol) was added to an ice-cooled stirred solution of 4-(2-hydroxyethyl)-7-iodo-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one (0.230 g, 0.75 mmol) and DIPEA (0.291 g, 2.25 mmol) in DCM (5 ml). The reaction mixture was stirred at room temperature under N2 for 1 h and then it was portioned between DCM and saturated NaHCO3 solution. The title compound was isolated by precipitation from the organic layer as a white solid (0.202 g, 0.52 mmol, 70%).

Workup

  1. temperaturecooled

Sources & evidence

ORD record
ord-2cb01231d1d44bb3966fe0e339f4a131
Source dataset
uspto-grants-2015_11
Patent number
US09181258B2

Reaction notes

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