Diisopropylethylamine → HCID 178516733, compound

HRID 2361218Notes

Reaction equation

HRID 2361218 reaction equation
Br[C:2]1[N:3]=[C:4]2[N:11]([CH:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[CH2:10][C:9](=[O:18])[NH:8][C:5]2=[N:6][CH:7]=1.Br[C:20]1[C:21]([NH:27][C:28](=O)CI)=[N:22][CH:23]=[C:24](Br)[N:25]=1.[CH:32](N(C(C)C)CC)(C)[CH3:33].O1CCC([NH2:47])CC1>C(#N)C>[NH:47]1[CH:28]=[N:27][C:21]([C:20]2[N:25]=[CH:24][C:23]([C:2]3[N:3]=[C:4]4[N:11]([CH:12]5[CH2:17][CH2:16][O:15][CH2:14][CH2:13]5)[CH2:10][C:9](=[O:18])[NH:8][C:5]4=[N:6][CH:7]=3)=[CH:33][CH:32]=2)=[N:22]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 4192234-AminotetrahydropyranHCID 58298325N-(3,5-dibromopyrazin-2-yl)-2-iodoacetamideHCID 866446486-Bromo-4-(tetrahydro-2H-pyran-4-yl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one

Product 1

HCID 178516733HCID 178516733, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-Bromo-4-(tetrahydro-2H-pyran-4-yl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one. To a solution of N-(3,5-dibromopyrazin-2-yl)-2-iodoacetamide (See Example 5.B) (6.6 g, 15.8 mmol) and diisopropylethylamine (4.0 g, 31.6 mmol) in acetonitrile (50 mL) was added tetrahydro-2H-pyran-4-amine (6.4 g, 63.2 mmol) and the mixture was stirred at ambient temperature for 16 h. The solvent was removed under reduced pressure and the residue which was purified by chromatography on silica gel (5-20% ethyl acetate in petroleum ether) to give the title compound (1.98 g, 40% yield). MS (ESI) m/z 313.1 [M+1]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue which was purified by chromatography on silica gel (5-20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-e85033fec7444efbbfe9036d0fc5881c
Source dataset
uspto-grants-2014_04
Patent number
US08686135B2

Reaction notes

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