Diisopropylethylamine → HCID 178516733, compound

HRID 454337Notes

Reaction equation

HRID 454337 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-c24c9e23b8c04cfa9b32d6a5242c8782
Source dataset
uspto-grants-2013_07
Patent number
US08492381B2

Reaction notes

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