6-Ethyl-3,5-dimethoxy-pyridine-2-carboxylic acid hydrazide → N[6-ethyl-3,5-dimethoxy-pyridine-2-carboxamidyl]-N'-(1-Methyl-1H-indol-5-yl)-thiourea

HRID 76100Notes

Reaction equation

HRID 76100 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]([C:9]([NH:11][NH2:12])=[O:10])[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[O:15][CH3:16])[CH3:2].[N:17]([C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[N:25]([CH3:29])[CH:24]=[CH:23]2)=[C:18]=[S:19]>C(O)C>[CH2:1]([C:3]1[N:8]=[C:7]([C:9]([NH:11][NH:12][C:18]([NH:17][C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[N:25]([CH3:29])[CH:24]=[CH:23]3)=[S:19])=[O:10])[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[O:15][CH3:16])[CH3:2]

Participants

4

Reactant 2

HCID 669866196-Ethyl-3,5-dimethoxy-pyridine-2-carboxylic acid hydrazideHCID 866216825-isothiocyanato-1-methyl-1H-indole

Product 1

HCID 86621683N[6-ethyl-3,5-dimethoxy-pyridine-2-carboxamidyl]-N'-(1-Methyl-1H-indol-5-yl)-thioureaYield 73.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A flask was charged with 6-ethyl-3,5-dimethoxy-pyridine-2-carboxylic acid hydrazide (34 mg; 0.15 mmol), 5-isothiocyanato-1-methyl-1H-indole (28 mg; 0.15 mmol) and ethanol (2 mL) and the mixture was heated at reflux for three hours. The reaction was then cooled, and the precipitate was filtered and dried to give N-[6-Ethyl-3,5-dimethoxy-pyridine-2-carboxamidyl]-N′-(1-Methyl-1H-indol-5-yl)-thiourea (44 mg; 0.11 mmol).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for three hours
  3. temperatureThe reaction was then cooled
  4. filtrationthe precipitate was filtered
  5. customdried

Sources & evidence

ORD record
ord-c1136b2b83144bfa95d1c2198c209054
Source dataset
uspto-grants-2014_09
Patent number
US08835464B2

Reaction notes

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