Acetonitrile → HCID 178462798, compound

HRID 1640322Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]2[N:11]([CH2:12][CH3:13])[CH2:10][C:9](=[O:14])[NH:8][C:5]2=[N:6][CH:7]=1.BrCC([NH:19][C:20]1[C:25](Br)=NC(Br)=[CH:22][N:21]=1)=O.C(N([CH:34]([CH3:36])[CH3:35])CC)(C)C.[ClH:37].[CH2:38](N)[CH3:39].C(#[N:43])C>>[ClH:37].[N:43]1[N:19]=[C:20]([C:25]2[CH:35]=[CH:34][C:36]([C:2]3[N:3]=[C:4]4[N:11]([CH2:12][CH3:13])[CH2:10][C:9](=[O:14])[NH:8][C:5]4=[N:6][CH:7]=3)=[CH:39][CH:38]=2)[NH:21][CH:22]=1

Participants

Reactant 5

HCID 6342Acetonitrile

HCID 11198Ethylamine hydrochloride

HCID 81531Diisopropylethylamine

HCID 582983072-bromo-N-(3,5-dibromopyrazin-2-yl)acetamide

HCID 866446546-Bromo-4-ethyl-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one

Product 1

HCID 178462798HCID 178462798, compoundYield 36%

Conditions

Temperature: 70 °C

Procedure

6-Bromo-4-ethyl-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one. To a solution of 2-bromo-N-(3,5-dibromopyrazin-2-yl)acetamide (See Example 4.A) (1 equiv) and diisopropylethylamine (3 equiv) in acetonitrile was added ethanamine hydrochloride (1.05 equiv). The solution was allowed to heat to 70° C. for 30 min. The solution was condensed under reduced pressure and purified using column chromatography (0-75% ethyl acetate in hexanes) to afford the title compound in 36% yield. MS (ESI) m/z 257.5 [M]+, 259.4 [M+2]+.

Workup

customcondensed under reduced pressure
custompurified

Sources & evidence

ORD record: ord-419899e506b94a5d8ecc5c47fd839179
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110578B2

Reaction notes

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