Water → HCID 69367896, compound

HRID 1295728Notes

Reaction equation

HRID 1295728 reaction equation
Cl[C:2]1[C:3]([N:8]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.C[C:23]([O-:26])([CH3:25])C.[K+].[OH2:28]>C(O)CO.O1CCOCC1>[OH:28][CH2:25][CH2:23][O:26][C:2]1[C:3]([N:8]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 865916251,1-Dimethylethyl 4-(3-chloro-2-pyrazinyl)hexahydro-1H-1,4-diazepine-1-carboxylate

Product 1

HCID 69367896HCID 69367896, compound

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred mixture of tert-butyl 4-(3-chloropyrazin-2-yl)-1,4-diazepane-1-carboxylate (2.5 g, 8.0 mmol; from Step 1) in ethylene glycol (8 mL) and dioxane (25 mL), was added t-BuOK (0.99 g, 8.8 mmol). The mixture was heated at 90° C. with condenser, under N2, overnight. Water (10 mL) was added to the light brown mixture and extracted with dichloromethane (3×20 mL). The organic phase was dried over MgSO4. The solution was filtered and the solvent evaporated. The residue was purified by chromatography on silica gel using toluene/EtOAc (2:3) as eluent. 1H NMR analysis supports the stated structure. Yield: 1.66 g (61%). HPLC purity: 100%. MS m/z 339 (M+H)+.

Workup

  1. extractionextracted with dichloromethane (3×20 mL)
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationThe solution was filtered
  4. customthe solvent evaporated
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-19d13c59aca0420ba63df62621e578ca
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

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