Azetidine → HCID 24856141, compound

HRID 545324Notes

Reaction equation

HRID 545324 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:25])[C:12]([S:15]([C:18]2[CH:19]=[N:20][C:21](Cl)=[CH:22][CH:23]=2)(=[O:17])=[O:16])([CH3:14])[CH3:13])[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[NH:32]1[CH2:35][CH2:34][CH2:33]1>O1CCOCC1>[N:32]1([C:21]2[N:20]=[CH:19][C:18]([S:15]([C:12]([CH3:14])([CH3:13])[C:11]([NH:10][C:7]3[S:8][CH:9]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[N:6]=3)=[O:25])(=[O:17])=[O:16])=[CH:23][CH:22]=2)[CH2:35][CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 10422AzetidineHCID 11430Potassium CarbonateHCID 24855903HCID 24855903, compound

Product 1

HCID 24856141HCID 24856141, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 79 mg (0.20 mmol) of N-(4-tert-butyl-thiazol-2-yl)-2-(6-chloro-pyridine-3-sulfonyl)-2-methyl-propionamide (example 265, Table 19) and 57.5 mg (0.42 mmol) of potassium carbonate in dioxane (2 mL) were added 27 μL (0.4 mmol) of azetidine. The reaction was heated in a sealed tube to 70° C. for 3 h. The solids were removed by filtration and rinsed with dioxane (5 mL). The filtrate was concentrated under reduced pressure and the residue purified by column chromatography (silica, eluent DCM, 5-10% ethyl acetate) to afford 67 mg of 2-(6-azetidin-1-yl-pyridine-3-sulfonyl)-N-(4-tert-butyl-thiazol-2-yl)-2-methyl-propionamide.

Workup

  1. customThe solids were removed by filtration
  2. washrinsed with dioxane (5 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue purified by column chromatography (silica, eluent DCM, 5-10% ethyl acetate)

Sources & evidence

ORD record
ord-945626f82d2f43d3b37afa1c07cc84b4
Source dataset
uspto-grants-2011_05
Patent number
US07935715B2

Reaction notes

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