Methylhydrazine → HCID 87303967, compound

HRID 401466Notes

Reaction equation

HRID 401466 reaction equation
[CH3:1][C:2]1[C:3]2[N:4]([C:14]([CH:17]=O)=[CH:15][N:16]=2)[CH:5]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:7]=1.[CH3:19][NH:20][NH2:21].[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[S:30](Cl)(=[O:32])=[O:31]>C(O)C>[F:29][C:26]1[CH:27]=[CH:28][C:23]([CH3:22])=[C:24]([S:30]([N:20]([CH3:19])/[N:21]=[CH:17]/[C:14]2[N:4]3[CH:5]=[C:6]([C:8]4[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=4)[CH:7]=[C:2]([CH3:1])[C:3]3=[N:16][CH:15]=2)(=[O:32])=[O:31])[CH:25]=1

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 1362865-Fluoro-2-methylbenzenesulphonyl chlorideHCID 86670594HCID 86670594, compound2×

Product 1

HCID 87303967HCID 87303967, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 8-methyl-6-(pyridin-3-yl)imidazo[1,2-a]pyridine-3-carbaldehyde (Intermediate 5, 80 mg, 0.337 mmol) in ethanol (10 mL) was added methyl hydrazine (0.035 mL, 0.675 mmol) at RT. The reaction mixture was heated at 80° C. for 4 hours. Ethanol was evaporated. Pyridine (5 mL) was added to this residue, followed by addition 2-methyl-5-fluoro benzene sulfonylchloride (105 mg, 0.506 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. Yield: 50 mg (27%); 1H NMR (CDCl3; 300 MHz): δ 9.41(s, 1H), 8.59 (s, 1H), 8.71 (d, 1H, J=3.9 Hz), 7.99 (s, 1H), 7.97 (m, 1H), 7.94 (s, 1H), 7.66 (dd, 1H, J=8.4, 2.7 Hz), 7.47 (m, 1H), 7.43 (s, 1H), 7.21 (m, 1H), 7.07 (m, 1H), 3.47 (s, 3H), 2.73 (s, 3H), 2.53 (s, 3H); MS: m/z 438 (M+1)+.

Workup

  1. customEthanol was evaporated
  2. additionPyridine (5 mL) was added to this residue
  3. customPyridine was evaporated
  4. additionWater was added to this residue
  5. extractionextracted with dichloromethane
  6. dry with materialOrganic layer was dried over sodium sulfate
  7. customwas purified by column chromatography (silica gel, 1.5% methanol in chloroform)

Sources & evidence

ORD record
ord-9c782a256ce448fb91fb5bb0d5c60910
Source dataset
uspto-grants-2014_06
Patent number
US08741932B2

Reaction notes

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