Triethylamine → 3-amino-6-bromo-N'-(3-methylthiophene-2-carbonyl)pyrazine-2-carbohydrazide

HRID 2204850

Reaction equation

HRID 2204850 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([OH:11])=O)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.[CH3:12][C:13]1[CH:17]=[CH:16][S:15][C:14]=1[C:18]([NH:20][NH2:21])=[O:19].CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.CCOC(C)=O.O>[NH2:1][C:2]1[C:3]([C:9]([NH:21][NH:20][C:18]([C:14]2[S:15][CH:16]=[CH:17][C:13]=2[CH3:12])=[O:19])=[O:11])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27600843-Methylthiophene-2-carbohydrazideHCID 185216003-Amino-6-bromopyrazine-2-carboxylic acid

Product 1

HCID 594723013-amino-6-bromo-N'-(3-methylthiophene-2-carbonyl)pyrazine-2-carbohydrazideYield 36.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 3-amino-6-bromo-pyrazine-2-carboxylic acid (13.26 g, 60.82 mmol) and 3-methylthiophene-2-carbohydrazide (10 g, 60.82 mmol) in DMF (95.00 mL) cooled in an ice bath was added Et3N (7.385 g, 10.17 mL, 72.98 mmol) followed by TBTU (23.43 g, 72.98 mmol) portionwise after complete addition, the reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was diluted with EtOAc (50 mL) and water (50 mL). The layers were separated and the organic extracts washed with water (1×50 mL) and brine (1×50 mL), dried over MgSO4 and concentrated to leave a brown solid (7.85 g, 36% yield) which was used directly in the next step without further purification.

Workup

  1. temperaturecooled in an ice bath
  2. additionportionwise after complete addition
  3. customThe layers were separated
  4. washthe organic extracts washed with water (1×50 mL) and brine (1×50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8f62e9a84923410fbc193a93a6540439
Source dataset
uspto-grants-2016_06
Patent number
US09365557B2

Linked notes

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