Sulfuric acid--4-methylpiperazine-1-carboximidamide (1/1) → HCID 25217526, compound

HRID 910672Notes

Reaction equation

HRID 910672 reaction equation
CN([CH:4]=[N:5][C:6]([C:8]1[S:9][CH:10]=[C:11]([Br:13])[CH:12]=1)=O)C.S(O)(O)(=O)=O.[CH3:19][N:20]1[CH2:25][CH2:24][N:23]([C:26]([NH2:28])=[NH:27])[CH2:22][CH2:21]1.CC([O-])(C)C.[K+]>O1CCOCC1>[Br:13][C:11]1[CH:12]=[C:8]([C:6]2[N:28]=[C:26]([N:23]3[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]3)[N:27]=[CH:4][N:5]=2)[S:9][CH:10]=1

Participants

5

Reactant 3

HCID 15564582Sulfuric acid--4-methylpiperazine-1-carboximidamide (1/1)HCID 23665647Potassium tert-butoxideHCID 67387591HCID 67387591, compound

Product 1

HCID 25217526HCID 25217526, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-bromo-thiophene-2-carboxylic acid dimethylamino-methyleneamide (261 mg, 1.0 mmol) in anhydrous 1,4-dioxane (8 mL) was added 4-methyl-piperazine-1-carboxamidine sulfate (95.6 mg, 0.25 mmol) and KOtBu (56.1 mg, 0.5 mmol). The resulting suspension was heated at reflux overnight under argon. After cooling, the reaction mixture was passed through a pad of diatomaceous earth, the filtrate was concentrated and the residue was purified by preparative TLC (2 M NH3 in MeOH/CH2Cl2) to yield the title compound as a yellowish solid.

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureat reflux overnight under argon
  3. temperatureAfter cooling
  4. concentrationthe filtrate was concentrated
  5. customthe residue was purified by preparative TLC (2 M NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-de15b777da28428495725fd4bda6ff60
Source dataset
uspto-grants-2011_09
Patent number
US08022209B2

Reaction notes

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