3-Methoxybenzylamine → HCID 136115967, compound

HRID 388108Notes

Reaction equation

HRID 388108 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=3)[C:9](=[O:12])[CH2:10][NH:11][C:5]2=[N:4][CH:3]=1.C[O:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)CN.C(N(C(C)C)CC)(C)C>CS(C)=O>[OH:23][C:24]1[CH:25]=[CH:26][C:29]([C:2]2[N:7]=[C:6]3[N:8]([CH2:13][C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=4)[C:9](=[O:12])[CH2:10][NH:11][C:5]3=[N:4][CH:3]=2)=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 211563-MethoxybenzylamineHCID 81531DiisopropylethylamineHCID 86626396HCID 86626396, compound

Product 1

HCID 136115967HCID 136115967, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

7-Bromo-1-(3-methoxybenzyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one. Methyl 2-(3,5-dibromopyrazin-2-ylamino) acetate (0.58 g, 1.8 mmol), 3-methoxybenzylamine (227 μL, 1.8 mmol), diisopropylethylamine (1 mL), and dimethylsulfoxide (1 mL) were heated to 100° C. for 3 d under nitrogen. The reaction was extracted with ethyl acetate and water. The organic layer was dried with magnesium sulfate, filtered and concentrated. The residue was purified on silica gel column (0-100% ethyl acetate in hexanes) to give the title compound (124 mg, 20% yield) as a pink solid. MS (ESI) m/z 349.0 [M+1]+.

Workup

  1. extractionThe reaction was extracted with ethyl acetate and water
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel column (0-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-0d9e3cd25fc04e16875f5b0423796361
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Reaction notes

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