Water → Tert-butyl 4-(7,7-dimethyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-B]pyrazin-5-YL)piperidine-1-carboxylate

HRID 707279Notes

Reaction equation

HRID 707279 reaction equation
Cl[C:2]1[C:3]([C:8]([CH3:26])([CH3:25])[C:9]([NH:11][CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=[O:10])=[N:4][CH:5]=[CH:6][N:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CS(C)=O>[CH3:25][C:8]1([CH3:26])[C:3]2[C:2](=[N:7][CH:6]=[CH:5][N:4]=2)[N:11]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[C:9]1=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 10796Cesium carbonateHCID 86694146Tert-butyl 4-(2-(3-chloropyrazin-2-YL)-2-methylpropanamido)piperidine-1-carboxylate

Product 1

HCID 86694147Tert-butyl 4-(7,7-dimethyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-B]pyrazin-5-YL)piperidine-1-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of tert-butyl 4-(2-(3-chloropyrazin-2-yl)-2-methylpropanamido)piperidine-1-carboxylate (2.8 g, 7.31 mmol) and cesium carbonate (7.15 g, 21.94 mmol) in DMSO (25 mL) was stirred at RT overnight. H2O was added, extracted with EtOAc (3×). The extracts were dried over MgSO4, concentrated, purified by ISCO (30% EtOAc/Hexanes) to give the title compound (2.15 g, 85%). MS (M+1): 347.1

Workup

  1. extractionextracted with EtOAc (3×)
  2. dry with materialThe extracts were dried over MgSO4
  3. concentrationconcentrated
  4. custompurified by ISCO (30% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-8fd4b22308994c319e72129f8ca77387
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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