Dimethylformamide → HCID 69364793, compound

HRID 1295703Notes

Reaction equation

HRID 1295703 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15](=[O:20])[NH:16][CH:17]=[CH:18][N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:22][CH:23]1[O:28][C:27]2[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=2[O:25][CH2:24]1.CN(C=O)C.C(=O)([O-])[O-].[K+].[K+]>CCOC(C)=O.O>[O:28]1[C:27]2[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=2[O:25][CH2:24][CH:23]1[CH2:22][N:16]1[CH:17]=[CH:18][N:19]=[C:14]([N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][CH2:12]2)[C:15]1=[O:20]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 953202-(Chloromethyl)-2,3-dihydro-1,4-benzodioxinHCID 590138923-(4-tert-Butoxycarbonyl-1-piperazinyl)-2(1H)-pyrazinone

Product 1

HCID 69364793HCID 69364793, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-(4-tert-butoxycarbonyl-1-piperazinyl)-2(1H)-pyrazinone (4.00 g, 14.3 mmol; from Example 48, Step 1), 2-chloromethyl-2,3-dihydro-benzo[1,4]dioxine (2.60 g, 14.3 mmol), DMF (10 g) and potassium carbonate (4.00 g, 28.9 mmol) was heated at 120° C. for 3 h. Water (100 g) and EtOAc (200 g) were added to the reaction mixture and the layers were separated. The organic layer was concentrated and the residue purified by chromatography on a MPLC column using a continuous gradient (0-100% EtOAc in heptane) as eluent. This provided 0.60 g (15%) of the title compound as an oil. 1H NMR analysis supports the stated structure.

Workup

  1. customthe layers were separated
  2. concentrationThe organic layer was concentrated
  3. customthe residue purified by chromatography on a MPLC column

Sources & evidence

ORD record
ord-49cfe89f3bc44adeb323ffd96ef214ee
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

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