Benzaldehyde → (E)-1-(3-amino-6-(4-(ethylsulfonyl)piperazin-1-yl)pyrazin-2-yl)-3-phenylprop-2-en-1-one

HRID 1959380Notes

Reaction equation

HRID 1959380 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[C:5]([C:21](=[O:23])[CH3:22])=[N:6][C:7]([N:10]2[CH2:15][CH2:14][N:13]([S:16]([CH2:19][CH3:20])(=[O:18])=[O:17])[CH2:12][CH2:11]2)=[CH:8][N:9]=1.[CH:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CO>[NH2:3][C:4]1[C:5]([C:21](=[O:23])/[CH:22]=[CH:24]/[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:6][C:7]([N:10]2[CH2:11][CH2:12][N:13]([S:16]([CH2:19][CH3:20])(=[O:18])=[O:17])[CH2:14][CH2:15]2)=[CH:8][N:9]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 667446911-(3-Amino-6-(4-(ethylsulfonyl)piperazin-1-yl)pyrazin-2-yl)ethanone

Product 1

HCID 46199875(E)-1-(3-amino-6-(4-(ethylsulfonyl)piperazin-1-yl)pyrazin-2-yl)-3-phenylprop-2-en-1-oneYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of NaOH in methanol (191.5 μl, of 10% w/v, 0.4787 mmol) was added to a solution of 1-(3-amino-6-(4-(ethylsulfonyl)piperazin-1-yl)pyrazin-2-yl)ethanone (150 mg, 0.4787 mmol) and benzaldehyde (50.80 mg, 48.66 μL, 0.4787 mmol) in methanol (4 mL) (1 mL of dichloromethane was added to aid solubility). The reaction mixture was allowed to stir overnight at RT and then filtered and washed with a small amount of methanol. The bright orange coloured solid was taken through crude to the next stage. (104.6 mg, 54% Yield). 1H NMR (400.0 MHz, DMSO) d 1.21 (t, 3H), 3.13 (q, 2H), 3.35-3.37 (m, 4H), 3.54-3.57 (m, 4H), 7.47-7.51 (m, 3H), 7.55 (br s, 2H), 7.72 (d, 1H), 7.79-7.81 (m, 2H), 8.28 (d, 1H), 8.41 (s, 1H) ppm; MS (ES+) 402.01

Workup

  1. filtrationfiltered
  2. washwashed with a small amount of methanol

Sources & evidence

ORD record
ord-928bc06de12f43bd95e1999d370c7724
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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