Diisopropylethylamine → 3-amino-6-(4-ethylsulfonylpiperazin-1-yl)-N-phenacyl-pyrazine-2-carboxamide

HRID 1959393Notes

Reaction equation

HRID 1959393 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[NH2:12][C:13]1[C:14]([C:30](O)=[O:31])=[N:15][C:16]([N:19]2[CH2:24][CH2:23][N:22]([S:25]([CH2:28][CH3:29])(=[O:27])=[O:26])[CH2:21][CH2:20]2)=[CH:17][N:18]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C.CCOC(C)=O.O>[NH2:12][C:13]1[C:14]([C:30]([NH:2][CH2:3][C:4](=[O:5])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:31])=[N:15][C:16]([N:19]2[CH2:20][CH2:21][N:22]([S:25]([CH2:28][CH3:29])(=[O:27])=[O:26])[CH2:23][CH2:24]2)=[CH:17][N:18]=1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)HCID 667445273-Amino-6-(4-(ethylsulfonyl)piperazin-1-yl)pyrazine-2-carboxylic acid

Product 1

HCID 667454513-amino-6-(4-ethylsulfonylpiperazin-1-yl)-N-phenacyl-pyrazine-2-carboxamideYield 67%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 22728543Water ethylacetateSolvent

Procedure

2-amino-1-phenyl-ethanone hydrochloride (136.1 mg, 0.7928 mmol) was added to a solution of 3-amino-6-(4-ethylsulfonylpiperazin-1-yl)pyrazine-2-carboxylic acid (250 mg, 0.7928 mmol) and DIPEA (512.3 mg, 690.4 μL, 3.964 mmol) in CH2Cl2 (3.332 mL) and DMF (833.2 μL) and the resulting solution stirred at room temperature for 1 hour. The reaction was diluted with EtOAc/water and the layers separated. The aqueous layer was extracted further with EtOAc (2×) and the combined organics washed with water (3×), dried (MgSO4) and concentrated in vacuo. The mixture was purified on silica gel by flash column chromatography (100% EtOAc) to afford the product (229 mg, 67% Yield). 1H NMR (CDCl3) d 1.28 (3H, t), 3.06 (2H, q), 3.51-3.53 (4H, m), 3.56-3.59 (4H, m), 4.95 (2H, d), 6.2 (2H, br s), 7.56 (2H, m), 7.68 (1H, m), 8.05 (3H, m), 8.65 (1H, m) ppm; MS (ES+) 433.0

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted further with EtOAc (2×)
  3. washthe combined organics washed with water (3×)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe mixture was purified on silica gel by flash column chromatography (100% EtOAc)

Sources & evidence

ORD record
ord-1359dd61b4354e79adf8a7df2f1491e3
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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