Water → HCID 22036419, compound

HRID 1789755Notes

Reaction equation

HRID 1789755 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[C:17]([O:22][CH2:23][CH2:24][OH:25])=[N:18][CH:19]=[CH:20][N:21]=2)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[Cl:26][C:27]1[C:32](Cl)=[N:31][CH:30]=[CH:29][N:28]=1.O>O1CCOCC1>[Cl:26][C:27]1[C:32]([O:25][CH2:24][CH2:23][O:22][C:17]2[C:16]([N:13]3[CH2:14][CH2:15][N:10]([C:8]([O:7][C:3]([CH3:6])([CH3:5])[CH3:4])=[O:9])[CH2:11][CH2:12]3)=[N:21][CH:20]=[CH:19][N:18]=2)=[N:31][CH:30]=[CH:29][N:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 785752,3-DichloropyrazineHCID 114160742-[3-(4-Tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol

Product 1

HCID 22036419HCID 22036419, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

NaH (50% in mineral oil; 0.153 g, 3.50 mmol) was added to a stirred solution of 2-[3-(4-tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol (1.00 g, 3.08 mmol; prepared in Example 52, Step 2) and 2,3-dichloropyrazine (1.0 g, 6.71 mmol) in dioxane (10 mL). The reaction was stirred in a sealed tube at 100° C. overnight. The reaction mixture was poured into water and extracted with diethyl ether. The ether phase was dried (MgSO4), concentrated and purified by column chromatography on silica using toluene/EtOAc (7:3) as eluent to give 0.823 g (61%) of the title product: Pos-EI-MS shows M+ and 14 ions supporting the stated structure. HRMS m/z calcd for C19H25CIN6O4 (M)+436.1626, found 436.1606.

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe ether phase was dried (MgSO4)
  3. concentrationconcentrated
  4. custompurified by column chromatography on silica

Sources & evidence

ORD record
ord-69620ec491364bf69d7ad8a18f9b26bf
Source dataset
uspto-grants-2006_07
Patent number
US07071180B2

Reaction notes

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