6-(6-(1-(Tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)pyridin-3-yl)-4-(tetrahydro-2H-pyran-4-yl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one → HCID 178516733, compound

HRID 1047258Notes

Reaction equation

HRID 1047258 reaction equation
O1CCCCC1[N:7]1[CH:11]=[N:10][C:9]([C:12]2[N:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]4[N:27]([CH:28]5[CH2:33][CH2:32][O:31][CH2:30][CH2:29]5)[CH2:26][C:25](=[O:34])[NH:24][C:21]4=[N:22][CH:23]=3)=[CH:14][CH:13]=2)=[N:8]1>Cl>[NH:7]1[CH:11]=[N:10][C:9]([C:12]2[N:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]4[N:27]([CH:28]5[CH2:29][CH2:30][O:31][CH2:32][CH2:33]5)[CH2:26][C:25](=[O:34])[NH:24][C:21]4=[N:22][CH:23]=3)=[CH:14][CH:13]=2)=[N:8]1

Participants

3

Reactant 1

HCID 666067256-(6-(1-(Tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)pyridin-3-yl)-4-(tetrahydro-2H-pyran-4-yl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one

Product 1

HCID 178516733HCID 178516733, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 6-(6-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)pyridin-3-yl)-4-(tetrahydro-2H-pyran-4-yl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one in methanolic hydrochloride solution was stirred at room temperature for 0.5 h. The solvent was evaporated under reduced pressure to give the crude product, which was washed with N,N-dimethylformamide to afford the title compound as a hydrochloride salt in 34% yield. 1H NMR (DMSO-d6, 400 MHz) δ (ppm) 11.44 (s, 1H), 9.30 (s, 1H), 8.59 (d, J=8.4 Hz, 1H), 8.46 (s, 1H), 8.22 (m, 2H), 4.70 (t, J=10 Hz, 1H), 4.16 (s, 1H), 3.99 (m, 4H), 3.51 (t, J=11.2 Hz, 2H), 1.86 (m, 2H), 1.69 (d, J=12.8 Hz, 2H); MS (ESI) m/z 379.1 [M+1]+.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customto give the crude product, which
  3. washwas washed with N,N-dimethylformamide

Sources & evidence

ORD record
ord-ecf26d7c4e8546fba0862c5b31c888a1
Source dataset
uspto-grants-2013_10
Patent number
US08569494B2

Reaction notes

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