Water → HCID 67365161, compound

HRID 1916598Notes

Reaction equation

HRID 1916598 reaction equation
C([O-])([O-])=O.[K+].[K+].[NH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.[Br:12][C:13]1[CH:14]=[CH:15][C:16]([NH:19][C:20](=[O:24])[CH:21](Cl)[CH3:22])=[N:17][CH:18]=1.O>CN(C=O)C>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([NH:19][C:20](=[O:24])[CH:21]([N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH3:22])=[N:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 43114359HCID 43114359, compound

Product 1

HCID 67365161HCID 67365161, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.01 g (29.0 mmol) K2CO3 and 1.19 mL (14.5 mmol) pyrrolidine are added successively to a solution of 3.5 g (13.3 mmol) N-(5-bromo-pyridin-2-yl)-2-chloro-propionamide in 50 mL DMF. The reaction is stirred for 3 days at RT and combined with 150 mL water. The aqueous phase is extracted twice with EtOAc and the organic phase is dried over MgSO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, gradient: PE/EtOAc 4:6 after EtOAc).

Workup

  1. extractionThe aqueous phase is extracted twice with EtOAc
  2. dry with materialthe organic phase is dried over MgSO4
  3. customis purified by chromatography (silica gel, gradient: PE/EtOAc 4:6 after EtOAc)

Sources & evidence

ORD record
ord-74ec5774591942e1be4c713c9c38df64
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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