N,N-Dimethylglycine → HCID 44124829, compound

HRID 1922311Notes

Reaction equation

HRID 1922311 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@H:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]2.Br[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=1.C([O-])([O-])=O.[Cs+].[Cs+].CN(C)CC(O)=O>CS(C)=O.[Cu]I>[CH3:25][C:22]1[CH:23]=[CH:24][C:19]([O:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[CH2:7][C@H:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]3)=[N:20][CH:21]=1

Participants

7

Reactant 4

HCID 673N,N-DimethylglycineHCID 10796Cesium carbonateHCID 5642162-Bromo-5-methylpyridineHCID 66857149(S)-N-(5-hydroxy-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

Product 1

HCID 44124829HCID 44124829, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

N-[(2S)-5-hydroxy-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide (50 mg, 0.196 mmol, Description 3), copper(I) iodide (41.0 mg, 0.215 mmol), 2-bromo-5-methylpyridine (33.7 mg, 0.196 mmol), Cs2CO3 (191 mg, 0.587 mmol) and N,N-dimethylglycine (24.23 mg, 0.235 mmol), in dimethyl sulfoxide (2 ml) were heated under microwave conditions for 30 minutes at 190° C. The reaction mixture was partitioned between EtOAc (10 ml) and water (5 ml). Aqueous was further extracted with DCM (10 ml). The organic solution was dried (Na2SO4) and evaporated under reduced pressure to yield the impure product as a dark brown oil. The product was purified by reverse phase chromatography using MDAP to give the title compound as a solid (17 mg).

Workup

  1. customThe reaction mixture was partitioned between EtOAc (10 ml) and water (5 ml)
  2. extractionAqueous was further extracted with DCM (10 ml)
  3. dry with materialThe organic solution was dried (Na2SO4)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7bc4ba6ea00049af9d1db61274f5c28d
Source dataset
uspto-grants-2012_05
Patent number
US08173820B2

Reaction notes

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