4-[3-azidomethyl-5-(3,5-dichlorophenylthio)-1-isopropyl-1H-pyrazol-4-ylmethyl]pyridine → [5-(3,5-Dichlorophenyl)sulfanyl-1-isopropyl-4-(4-pyridylmethyl)pyrazol-3-yl]methanamine

HRID 1862468Notes

Reaction equation

HRID 1862468 reaction equation
[N:1]([CH2:4][C:5]1[C:9]([CH2:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[C:8]([S:17][C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=2)[N:7]([CH:26]([CH3:28])[CH3:27])[N:6]=1)=[N+]=[N-]>C(OCC)(=O)C.[Pd]>[Cl:25][C:20]1[CH:19]=[C:18]([S:17][C:8]2[N:7]([CH:26]([CH3:28])[CH3:27])[N:6]=[C:5]([CH2:4][NH2:1])[C:9]=2[CH2:10][C:11]2[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=2)[CH:23]=[C:22]([Cl:24])[CH:21]=1

Participants

4

Reactant 1

HCID 867588894-[3-azidomethyl-5-(3,5-dichlorophenylthio)-1-isopropyl-1H-pyrazol-4-ylmethyl]pyridine

Product 1

HCID 514443[5-(3,5-Dichlorophenyl)sulfanyl-1-isopropyl-4-(4-pyridylmethyl)pyrazol-3-yl]methanamineYield 54.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution containing 120 mg of 4-[3-Azidomethyl-5-(3,5-dichloro-phenylsulfanyl)-1-isopropyl-1H-pyrazol-4-ylmethyl]-pyridine in 5 ml of ethyl acetate was treated with 20 mg of 10% palladium on charcoal and then hydrogenated at atmospheric pressure for 2.0 h. The mixture was filtered and then the solvent was removed under reduced pressure. The residue was purified by flash chromatography on silica gel using methanol/dichloromethane (1:9) for the elution to give 61 mg of 5-(3,5-dichlorophenylthio)-1-isopropyl-4-[(4-pyridyl)methyl]-1H-pyrazole-3-methylamine as a pale yellow oil. Mass spectrum (ESI) m/z 407 [M+H]+. 1H NMR (DMSO) 1.30 (d, 6H), 3.72 (s, 2H), 3.90 (s, 2H), 4.70 (m, 1H), 6.78 (s, 2H), 7.10 (d, 2H), 7.37 (s, 1H), 8.30 (d, 2H).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified by flash chromatography on silica gel
  4. washfor the elution

Sources & evidence

ORD record
ord-088d8f7f4dbb4497b217018244de7a28
Source dataset
uspto-grants-2003_03
Patent number
US06538015B1

Reaction notes

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