Methylhydrazine → HCID 87304354, compound

HRID 401467Notes

Reaction equation

HRID 401467 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]2[N:14]([C:16]([CH:19]=O)=[CH:17][N:18]=2)[CH:15]=1.[CH3:21][NH:22][NH2:23].[CH3:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=1[S:32](Cl)(=[O:34])=[O:33]>C(O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]2[N:14]([C:16](/[CH:19]=[N:23]/[N:22]([CH3:21])[S:32]([C:26]3[CH:27]=[C:28]([F:31])[CH:29]=[CH:30][C:25]=3[CH3:24])(=[O:33])=[O:34])=[CH:17][N:18]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 1362865-Fluoro-2-methylbenzenesulphonyl chlorideHCID 86670612HCID 86670612, compound2×

Product 1

HCID 87304354HCID 87304354, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-(1H-indol-2-yl)imidazo[1,2-a]pyridine-3-carbaldehyde (Intermediate 6, 115 mg, 0.3691 mmol) in ethanol (10 mL) was added methyl hydrazine (0.04 mL, 0.7395 mmol) at RT. The reaction mixture was heated at 80° C. for 4 h. Ethanol was evaporated. Pyridine (5 mL) was added to this residue, followed by addition of 2-methyl-5-fluoro benzene sulfonylchloride (0.07 mL, 0.5535 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: 28 mg (17%); 1H NMR (DMSO-d6; 500 MHz): δ 11.83 (s, 1H), 9.09 (s, 1H), 9.81 (s, 1H), 8.34 (s, 1H), 8.27 (d, 1H, J=9.5 Hz), 8.08 (d, 1H, J=9.5 Hz), 7.74 (d, 1H, J=6.5 Hz), 7.61 (d, 1H, J=8 Hz), 7.43 (m, 3H), 7.18 (t, 1H, J=8), 7.07 (t, 1H, J=7.5 Hz), 6.91 (s, 1H), 3.48 (s, 3H); MS: m/z 460 (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. customevaporated
  8. customThe crude product was purified by column chromatography (Silica gel, 1.5% methanol in chloroform)

Sources & evidence

ORD record
ord-214ebe82e4be4986881cecd1d710d29c
Source dataset
uspto-grants-2014_06
Patent number
US08741932B2

Reaction notes

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