1,4-Cyclohexadiene → HCID 86663238, compound

HRID 2070719Notes

Reaction equation

HRID 2070719 reaction equation
Br[C:2]1[C:3](=[O:20])[N:4]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=2[CH3:19])[C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6](Br)[N:7]=1.[CH2:21]([NH:28][CH2:29][CH2:30][N:31]([CH3:33])[CH3:32])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)C(C)C)(C)C.C1CC=CCC=1>[Pd].O1CCCC1>[CH3:32][N:31]([CH3:33])[CH2:30][CH2:29][N:28]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:2]1[C:3](=[O:20])[N:4]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=2[CH3:19])[C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:6][N:7]=1

Participants

7

Reactant 4

HCID 123431,4-CyclohexadieneHCID 660291,2-Ethanediamine, N1,N1-dimethyl-N2-(phenylmethyl)-HCID 81531DiisopropylethylamineHCID 66688740methyl 3-(3,5-dibromo-2-oxopyrazin-1(2H)-yl)-4-methylbenzoate

Product 1

HCID 86663238HCID 86663238, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(3,5-dibromo-2-oxo-2H-pyrazin-1-yl)-4-methyl-benzoic acid, methyl ester (Example 1b, 129 mg), N′-benzyl-N,N-dimethylethylenediamine (0.1 mL), N,N-diisopropylethylamine (0.1 mL) and tetrahydrofuran (1 mL) was heated within a microwave for 15 minutes at 100° C. before being cooled to room temperature. The mixture was transferred to a mixture of palladium on carbon (10%, 50 mg) and tetrahydrofuran (1 mL) and 1,4-cyclohexadiene (1 mL) was added. The mixture was heated within a microwave for 60 minutes at 120° C. before being cooled to room temperature. The mixture was filtered and the filtrated concentrated in vacuo. Purification by preparative HPLC (Gemini column, 0.1% ammonia: acetonitrile eluent) afforded the title compound as a solid (50 mg).

Workup

  1. temperaturebefore being cooled to room temperature
  2. additionwas added
  3. temperatureThe mixture was heated within a microwave for 60 minutes at 120° C.
  4. temperaturebefore being cooled to room temperature
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrated concentrated in vacuo
  7. customPurification by preparative HPLC (Gemini column, 0.1% ammonia: acetonitrile eluent)

Sources & evidence

ORD record
ord-f4811d30120c46aa86bb86686bb24dd6
Source dataset
uspto-grants-2012_10
Patent number
US08299246B2

Reaction notes

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