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

HRID 1959376
Notes
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Reaction equation

HRID 1959376 reaction equation
[NH2:1][C:2]1[C:3]([C:19]([OH:21])=O)=[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.Cl.[CH3:23][O:24][NH:25][CH3:26].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.O>[NH2:1][C:2]1[C:3]([C:19]([N:25]([O:24][CH3:23])[CH3:26])=[O:21])=[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 667445273-Amino-6-(4-(ethylsulfonyl)piperazin-1-yl)pyrazine-2-carboxylic acid

Product 1

HCID 866620733-amino-6-(4-(ethylsulfonyl)piperazin-1-yl)-N-methoxy-N-methylpyrazine-2-carboxamide
Yield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-amino-6-(4-ethylsulfonylpiperazin-1-yl)pyrazine-2-carboxylic acid (1 g, 3.171 mmol), N-methoxymethanamine hydrochloride (371.2 mg, 3.805 mmol) and triethylamine (705.9 mg, 972.3 μL 6.976 mmol) were dissolved in DMF (10 mL) and treated with TBTU (1.527 g, 4.756 mmol). The mixture was allowed to stir at ambient temperature for 1 hour. The reaction was treated with water, extracted with EtOAc (4×), and the organics separated, dried (MgSO4) and concentrated. The resultant residue was purified on silica gel by flash column chromatography (0-100% EtOAc/Petrol) to afford the title compound as a yellow solid (864 mg, 76% Yield). 1H NMR (400.0 MHz, DMSO) d 1.21 (t, 3H), 3.10 (q, 2H), 3.27-3.30 (m, 4H), 3.34 (s, 3H), 3.38-3.40 (m, 4H), 3.68 (s, 3H), 5.87 (br s, 2H) and 7.99 (s, 1H) ppm; MS (ES+) 359.0

Workup

  1. extractionextracted with EtOAc (4×)
  2. dry with materialthe organics separated, dried (MgSO4)
  3. concentrationconcentrated
  4. customThe resultant residue was purified on silica gel by flash column chromatography (0-100% EtOAc/Petrol)

Sources & evidence

ORD record
ord-53c32377c07240209d6f963b158c3e83
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08410112B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes