Water → HCID 46917074, compound

HRID 2045917Notes

Reaction equation

HRID 2045917 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].Cl[CH2:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[CH:28]=[N:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=2)[CH:14]=1)=[O:11].O>CN(C=O)C>[N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:27]=[CH:28][C:19]=1[C:15]1[CH:14]=[C:13]([NH:12][C:10](=[O:11])[CH2:9][N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 14854332-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide

Product 1

HCID 46917074HCID 46917074, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1,2,4-triazole (18 mg, 0.258 mmol) in DMF (1 mL), NaH (11.5 mg 60% in mineral oil, 0.282 mmol) was added and the slurry was stirred at room temperature for 5 min. To the slurry, 2-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide (70 mg, 0.235 mmol) in DMF (2 mL) was added at room temperature at stirred for 2 days. Water (5 mL) was added and the reaction mixture was extracted with ethyl acetate (25 mL). The organic phase was dried over MgSO4, the solvent evaporate in vacuo, and the resulting solid was purified by preparative LCMS to afford N-[3-(quinoxalin-2-yl)phenyl]-2-(1H-1,2,4-triazol-1-yl)acetamide (56 mg, 72% yield). LCMS calculated for C18H14N6O (M+H): 331.34. found 331.11. 1H-NMR (DMSO-d6, 400 Mhz) δH: 10.65 (1H, br. s), 9.52 (1H, s), 8.58 (1H, s), 8.55 (1H, m), 8.12 (1H, m), 8.10 (1H, d, J=7 Hz), 8.04 (1H, s), 7.98-7.80 (3H, m), 7.58 (1H, m), 5.21 (2H, s).

Workup

  1. stirringat stirred for 2 days
  2. extractionthe reaction mixture was extracted with ethyl acetate (25 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. customthe solvent evaporate in vacuo
  5. customthe resulting solid was purified by preparative LCMS

Sources & evidence

ORD record
ord-1be8b692f37e40cc9956f11e38a9f64d
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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