Hydrochloric Acid → HCID 178462798, compound

HRID 1890886Notes

Reaction equation

HRID 1890886 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[N:8][CH:9]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4[N:23](C5CCCCO5)[CH:22]=[N:21][N:20]=4)=[CH:15][CH:14]=3)[N:11]=2)[NH:6][C:5](=[O:30])[CH2:4]1)[CH3:2].[ClH:31]>C(O)C.O1CCOCC1>[ClH:31].[N:21]1[N:20]=[C:19]([C:16]2[CH:17]=[CH:18][C:13]([C:10]3[N:11]=[C:12]4[N:3]([CH2:1][CH3:2])[CH2:4][C:5](=[O:30])[NH:6][C:7]4=[N:8][CH:9]=3)=[CH:14][CH:15]=2)[NH:23][CH:22]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 666071504-Ethyl-6-(4-(4-(tetrahydro-2H-pyran-2-yl)-4H-1,2,4-triazol-3-yl)phenyl)-3,4-dihydro-pyrazino[2,3-b]pyrazin-2(1H)-one

Product 1

HCID 178462798HCID 178462798, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

4-Ethyl-6-(4-(4-(tetrahydro-2H-pyran-2-yl)-4H-1,2,4-triazol-3-yl)phenyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one in ethanol was treated with 2 N hydrogen chloride in dioxane. The solution was stirred at 75° C. for 1 h. The solution was condensed partially and cooled. Cold ethanol was added to the slurry and the resulting precipitate filtered and washed with additional cold ethanol followed by hexanes to afford the title compound as the hydrochloride salt in 82% yield. 1H NMR (400 MHz, METHANOL-d4) δ (ppm) 9.18 (s, 1H), 8.22 (d, J=8.59 Hz, 2H), 8.04-8.09 (m, 3H), 7.66-7.74 (m, 1H), 7.58-7.64 (m, 1H), 4.24 (s, 2H), 3.74 (q, J=7.03 Hz, 2H), 1.29 (t, J=7.03 Hz, 4H), 0.79-0.98 (m, 4H); MS (ESI) m/z 322.2 [M+1]+.

Workup

  1. customcondensed partially
  2. temperaturecooled
  3. filtrationthe resulting precipitate filtered
  4. washwashed with additional cold ethanol

Sources & evidence

ORD record
ord-50cac8c9952648d7af2354dd107d41d5
Source dataset
uspto-grants-2013_08
Patent number
US08507492B2

Reaction notes

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