N,N-Dimethylglycine → HCID 44124830, compound

HRID 1922312Notes

Reaction equation

HRID 1922312 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]=[C:23]([CH3:25])[CH:22]=[CH:21][N:20]=1.C([O-])([O-])=O.[Cs+].[Cs+].CN(C)CC(O)=O>CS(C)=O.[Cu]I>[CH3:25][C:23]1[CH:22]=[CH:21][N:20]=[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)[CH:24]=1

Participants

7

Reactant 4

HCID 673N,N-DimethylglycineHCID 10796Cesium carbonateHCID 27340872-Bromo-4-methylpyridineHCID 66857149(S)-N-(5-hydroxy-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

Product 1

HCID 44124830HCID 44124830, 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-4-methylpyridine (0.022 ml, 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 (10 ml). Aqueous was further extracted with DCM (10 ml). The organic solution was dried over MgSO4 and evaporated under reduced pressure to yield the impure product as a dark brown oil. The product was purified by reverse phase chromatography using the MDAP to give the title compound as a white solid (5 mg).

Workup

  1. customThe reaction mixture was partitioned between EtOAc (10 ml) and water (10 ml)
  2. extractionAqueous was further extracted with DCM (10 ml)
  3. dry with materialThe organic solution was dried over MgSO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-83114e8ec9af4870b3d7d3096b39f959
Source dataset
uspto-grants-2012_05
Patent number
US08173820B2

Reaction notes

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