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 454344Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:13][CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[C:9](=[O:12])[CH2:10][NH:11][C:5]2=[N:4][CH:3]=1.Br[C:22]1[N:23]=[C:24]([NH:35][CH2:36][CH2:37][CH:38]2[CH2:43][CH2:42]OCC2)C(NCC(OCC)=O)=NC=1.Cl>C(O)C>[NH:35]1[C:24]2=[N:23][CH:22]=[C:42]([C:2]3[N:7]=[C:6]4[N:8]([CH2:13][CH2:14][CH:15]5[CH2:20][CH2:19][O:18][CH2:17][CH2:16]5)[C:9](=[O:12])[CH2:10][NH:11][C:5]4=[N:4][CH:3]=3)[CH:43]=[C:38]2[CH:37]=[CH:36]1

Participants

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

concentrationThe reaction mixture was concentrated
custompurified

Sources & evidence

ORD record: ord-795be5966b414b4ab502df1b2688ee20
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492381B2

Reaction notes

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