Hydrochloric Acid → 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 1525499Notes

Reaction equation

HRID 1525499 reaction equation
C(O[C:4](=[O:23])[CH2:5][NH:6][C:7]1[C:12]([NH:13][CH2:14][CH2:15][CH:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[N:11][C:10](Br)=[CH:9][N:8]=1)C.Br[C:25]1[N:30]=[C:29]2[N:31]([CH2:36][CH2:37][CH:38]3[CH2:43][CH2:42]OCC3)C(=O)CNC2=NC=1.Cl>C(O)C>[NH:31]1[C:29]2=[N:30][CH:25]=[C:42]([C:10]3[N:11]=[C:12]4[N:13]([CH2:14][CH2:15][CH:16]5[CH2:17][CH2:18][O:19][CH2:20][CH2:21]5)[C:4](=[O:23])[CH2:5][NH:6][C:7]4=[N:8][CH:9]=3)[CH:43]=[C:38]2[CH:37]=[CH:36]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118218518HCID 118218518, compound

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)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

7-Bromo-1-(2-(tetrahydro-2H-pyran-4-yl)ethyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one Ethyl 2-(5-bromo-3-(2-(tetrahydro-2H-pyran-4-yl)ethylamino)pyrazin-2-ylamino)acetate (0.5 g, 1.291 mmol) and hydrochloric acid (6 M in water, 0.215 mL, 1.291 mmol) were combined in ethanol (2 mL) and the resulting mixture was heated in a Biotage Emrys Optimizer microwave reactor at 100° C. for 2400 s. The reaction mixture was concentrated and purified using silica gel chromatography (33% ethyl acetate in hexanes) to yield the title compound (quantitative yield). MS (ESI) m/z 341.1 [M]+, 343.1 [M+2]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified

Sources & evidence

ORD record
ord-994d6de26ae74d9694f9e7d676bb8c2d
Source dataset
uspto-grants-2015_07
Patent number
US09079900B2

Reaction notes

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