Hydrazine hydrate (1:1) → 4-(4-cyclopropyl-1H-imidazol-1-yl)-N-(5-(hydrazinecarbonyl)thiophen-3-yl)picolinamide

HRID 1423333Notes

Reaction equation

HRID 1423333 reaction equation
[CH:1]1([C:4]2[N:5]=[CH:6][N:7]([C:9]3[CH:14]=[CH:13][N:12]=[C:11]([C:15]([NH:17][C:18]4[CH:19]=[C:20]([C:23](OC)=[O:24])[S:21][CH:22]=4)=[O:16])[CH:10]=3)[CH:8]=2)[CH2:3][CH2:2]1.O.[NH2:28][NH2:29]>C(O)C>[CH:1]1([C:4]2[N:5]=[CH:6][N:7]([C:9]3[CH:14]=[CH:13][N:12]=[C:11]([C:15]([NH:17][C:18]4[CH:19]=[C:20]([C:23]([NH:28][NH2:29])=[O:24])[S:21][CH:22]=4)=[O:16])[CH:10]=3)[CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58035644methyl 4-(4-(4-cyclopropyl-1H-imidazol-1-yl)picolinamido)thiophene-2-carboxylate

Product 1

HCID 580356454-(4-cyclopropyl-1H-imidazol-1-yl)-N-(5-(hydrazinecarbonyl)thiophen-3-yl)picolinamideYield 103.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 4-(4-(4-cyclopropyl-1H-imidazol-1-yl)picolinamido)thiophene-2-carboxylate (380 mg, 1.0 mmol) was dissolved in ethanol, hydrazine hydrate (0.26 mL, 5.2 mmol) was added, and the reaction was refluxed overnight. The solvent was removed under reduced pressure, and the solids were suspended in acetonitrile and filtered to afford 380 mg of 4-(4-cyclopropyl-1H-imidazol-1-yl)-N-(5-(hydrazinecarbonyl)thiophen-3-yl)picolinamide as a white solid. M+1=369.1

Workup

  1. temperaturethe reaction was refluxed overnight
  2. customThe solvent was removed under reduced pressure
  3. filtrationfiltered

Sources & evidence

ORD record
ord-7789bdba9d764fb9b307de94961dac34
Source dataset
uspto-grants-2015_01
Patent number
US08927582B2

Reaction notes

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