7-(5-Fluoro-2-methyl-4-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)phenyl)-1-isopropyl-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one → HCID 178423430, compound

HRID 1890851Notes

Reaction equation

HRID 1890851 reaction equation
[F:1][C:2]1[C:3]([C:23]2[N:27]=[CH:26][N:25](C3CCCCO3)[N:24]=2)=[CH:4][C:5]([CH3:22])=[C:6]([C:8]2[N:13]=[C:12]3[N:14]([CH:19]([CH3:21])[CH3:20])[C:15](=[O:18])[CH2:16][NH:17][C:11]3=[N:10][CH:9]=2)[CH:7]=1>Cl.C(=O)(O)[O-].[Na+]>[F:1][C:2]1[C:3]([C:23]2[N:27]=[CH:26][NH:25][N:24]=2)=[CH:4][C:5]([CH3:22])=[C:6]([C:8]2[N:13]=[C:12]3[N:14]([CH:19]([CH3:21])[CH3:20])[C:15](=[O:18])[CH2:16][NH:17][C:11]3=[N:10][CH:9]=2)[CH:7]=1

Participants

4

Reactant 1

HCID 666075107-(5-Fluoro-2-methyl-4-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)phenyl)-1-isopropyl-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one

Product 1

HCID 178423430HCID 178423430, compoundYield 46.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 7-(5-fluoro-2-methyl-4-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)phenyl)-1-isopropyl-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one (200 mg, 0.44 mmol) in methanolic hydrochloride solution (20 mL, 2 M) was stirred for 5 h at room temperature. The reaction was diluted with saturated aqueous sodium bicarbonate solution (25 mL) and the aqueous mixture was extracted with ethyl acetate (25 mL×2). The organic phase was dried over sodium sulfate, filtered, evaporated under reduced pressure and purified on silica gel column (50-100% ethyl acetate in petroleum ether). The desired fractions were combined and concentrated under reduced pressure to give the title compound (75 mg, 46% yield). 1H NMR (DMSO-d6, 400 MHz): δ (ppm) 14.25 (br. s., 1H), 8.20 (br. s., 1H), 7.90 (m, 2H), 7.58 (s, 1H), 7.35 (s, 1H), 5.24 (m, 1H), 4.10 (s, 2H), 2.43 (s, 3H), 1.44 (d, J=7.2, 6H); MS (ESI) m/z 368.2 [M+1]+.

Workup

  1. extractionthe aqueous mixture was extracted with ethyl acetate (25 mL×2)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. custompurified on silica gel column (50-100% ethyl acetate in petroleum ether)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8be49caef8b2441688aa0431c50ef386
Source dataset
uspto-grants-2013_08
Patent number
US08507492B2

Reaction notes

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