2-(Oxan-4-yl)ethan-1-amine → 7-(1H-Pyrrolo[2,3-b]pyridin-5-yl)-1-(2-(tetrahydro-2h-pyran-4-yl)ethyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one

HRID 1525498Notes

Reaction equation

HRID 1525498 reaction equation
C(O[C:4](=[O:15])[CH2:5][NH:6][C:7]1[C:12](Br)=[N:11][C:10](Br)=[CH:9][N:8]=1)C.Br[C:17]1[N:18]=[C:19]([NH:30][CH2:31][CH2:32][CH:33]2[CH2:38][CH2:37]OCC2)C(NCC(OCC)=O)=NC=1.[O:39]1[CH2:44][CH2:43][CH:42]([CH2:45][CH2:46][NH2:47])[CH2:41][CH2:40]1>CS(C)=O>[NH:30]1[C:19]2=[N:18][CH:17]=[C:37]([C:10]3[N:11]=[C:12]4[N:47]([CH2:46][CH2:45][CH:42]5[CH2:43][CH2:44][O:39][CH2:40][CH2:41]5)[C:4](=[O:15])[CH2:5][NH:6][C:7]4=[N:8][CH:9]=3)[CH:38]=[C:33]2[CH:32]=[CH:31]1

Participants

4

Reactant 2

HCID 27731982-(Oxan-4-yl)ethan-1-amineHCID 118218516Ethyl 2-(5-bromo-3-(2-(tetrahydro-2H-pyran-4-yl)ethylamino)pyrazin-2-ylamino)acetate Ethyl 2-(3,5-dibromopyrazin-2-ylamino)acetate

Product 1

HCID 594530677-(1H-Pyrrolo[2,3-b]pyridin-5-yl)-1-(2-(tetrahydro-2h-pyran-4-yl)ethyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-oneYield 44.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

Ethyl 2-(5-bromo-3-(2-(tetrahydro-2H-pyran-4-yl)ethylamino)pyrazin-2-ylamino)acetate Ethyl 2-(3,5-dibromopyrazin-2-ylamino)acetate (See Example 6.B) (1.0 g, 2.95 mmol) and 2-(tetrahydro-2H-pyran-4-yl)ethanamine (0.381 g, 2.95 mmol) were placed in a microwave vial, dimethylsulfoxide (2 mL) was added and the resulting mixture was heated in a Biotage Emrys Optimizer microwave reactor at 150° C. for 3600 s. The crude reaction mixture was purified using silica gel chromatography (33% ethyl acetate in hexanes) to yield the title compound (0.5 g, 1.3 mmol, 44% yield). MS (ESI) m/z 387.1 [M]+, 389.1 [M+2]+.

Workup

  1. additionwas added
  2. customThe crude reaction mixture
  3. customwas purified

Sources & evidence

ORD record
ord-bbb57764939a46508bd7f36b96f295fd
Source dataset
uspto-grants-2015_07
Patent number
US09079900B2

Reaction notes

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