Pyridine → HCID 59732931, compound

HRID 131889Notes

Reaction equation

HRID 131889 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:5]=[C:6]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]=2[C:20]([CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)=[O:21])=[O:11])[S:7][CH:8]=1.[CH3:27][S:28](Cl)(=[O:30])=[O:29].N1C=CC=CC=1>C(Cl)Cl>[CH:22]1([C:20]([C:14]2[CH:15]=[C:16]([CH3:19])[CH:17]=[CH:18][C:13]=2[NH:12][C:10](=[O:11])[NH:9][C:6]2[S:7][CH:8]=[C:4]([CH2:3][CH2:2][NH:1][S:28]([CH3:27])(=[O:30])=[O:29])[N:5]=2)=[O:21])[CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 59732818HCID 59732818, compound

Product 1

HCID 59732931HCID 59732931, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-[4-(amino-ethyl)-thiazol-2-yl]-3-(2-cyclopentanecarbonyl-4-methyl-phenyl)-urea (0.05 g, 0.13 mmol) in 10 mL DCM at 0° C. was added methanesulfonyl chloride (0.02 g, 0.13 mmol) followed by pyridine (0.02 g, 0.21 mmol). The reaction was stirred at ambient temperature overnight, concentrated and purified by flash chromatography on silica gel with 20–50% EtOAc/hexane to obtain the product as white solid in 75% yield.

Workup

  1. concentrationconcentrated
  2. custompurified by flash chromatography on silica gel with 20–50% EtOAc/hexane

Sources & evidence

ORD record
ord-45ac53bf3c8d4efa8a1f7a6754bde5c8
Source dataset
uspto-grants-2008_06
Patent number
US07384967B2

Reaction notes

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