Methylhydrazine → HCID 67197081, compound

HRID 401464Notes

Reaction equation

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

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 6-(pyridin-3-yl)imidazo[1,2-a]pyridine-3-carbaldehyde (Intermediate 1, 70 mg, 0.31 mmol) in ethanol (3 mL) was added methyl hydrazine (17 mg, 0.47 mmol) at RT. The reaction was heated at 85° C. for 3 h. Ethanol was evaporated. Pyridine (2 mL) was added to this residue, followed by addition of benzene sulfonylchloride (83 mg, 0.47 mmol). The reaction mixture was stirred at RT overnight. Pyridine was evaporated. Water was added to this residue and extracted with dichloromethane. Organic layer was dried over sodium sulfate and evaporated. The crude product was purified by column chromatography (silica gel, 1.5% methanol in chloroform) to obtain the title compound.

Workup

customEthanol was evaporated
additionPyridine (2 mL) was added to this residue
customPyridine was evaporated
additionWater was added to this residue
extractionextracted with dichloromethane
dry with materialOrganic layer was dried over sodium sulfate
customevaporated
customThe crude product was purified by column chromatography (silica gel, 1.5% methanol in chloroform)

Sources & evidence

ORD record: ord-fab4bf0c9e2043fa89dbd65dc8dc27b8
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741932B2

Reaction notes

Loading…