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3-amino-6-(4-(ethylsulfonyl)piperazin-1-yl)-N-methoxy-N-methylpyrazine-2-carboxamide → 1-(3-Amino-6-(4-(ethylsulfonyl)piperazin-1-yl)pyrazin-2-yl)ethanone

HRID 1959377
Notes
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Reaction equation

HRID 1959377 reaction equation
[NH2:1][C:2]1[C:3]([C:19](N(OC)C)=[O:20])=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:6][N:7]=1.[CH3:25][Mg+].[Br-]>C1COCC1>[NH2:1][C:2]1[C:3]([C:19](=[O:20])[CH3:25])=[N:4][C:5]([N:8]2[CH2:9][CH2:10][N:11]([S:14]([CH2:17][CH3:18])(=[O:15])=[O:16])[CH2:12][CH2:13]2)=[CH:6][N:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 866620733-amino-6-(4-(ethylsulfonyl)piperazin-1-yl)-N-methoxy-N-methylpyrazine-2-carboxamideHCID 178418689HCID 178418689, compound2×

Product 1

HCID 667446911-(3-Amino-6-(4-(ethylsulfonyl)piperazin-1-yl)pyrazin-2-yl)ethanoneYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

3-amino-6-(4-(ethylsulfonyl)piperazin-1-yl)-N-methoxy-N-methylpyrazine-2-carboxamide (864 mg, 2.411 mmol) was dissolved in THF (10 mL) and cooled to −20° C. under nitrogen. MeMgBr (2.411 mL of 3 M, 7.233 mmol) was added dropwise and the reaction was left to stir at this temperature for 15 minutes after which time the reaction was allowed to slowly warm to ambient temperature. A further MeMgBr (803.7 μL of 3 M, 2.411 mmol) was added and analysis showed after 10 minutes showed no SM remaining. The mixture was quenched with 10 mL 1M HCl, stirred for 5 mins and then extracted with EtOAc (3×), dried (MgSO4), filtered and the solvent removed in vacuo to give the product as an orange solid (510 mg, 68% Yield). 1H NMR (400.0 MHz, DMSO) d 1.23 (t, 3H), 2.54 (s, 3H), 3.11 (q, 2H), 3.30-3.32 (m, 4H), 3.47-3.49 (m, 4H), 7.42 (br s, 2H) and 8.34 (s, 1H) ppm; MS (ES+) 314.0

Workup

  1. waitthe reaction was left
  2. temperatureto slowly warm to ambient temperature
  3. waitanalysis showed after 10 minutes
  4. customThe mixture was quenched with 10 mL 1M HCl
  5. stirringstirred for 5 mins
  6. extractionextracted with EtOAc (3×)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-fb7aebee5f5f401fa508a56a30160da8
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08410112B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes