Aziridine → azetidin-1-yl(1-{4-[(1-cyclobutylpiperidin-4-yl)oxy]phenyl}-1H-pyrrol-3-yl)methanone

HRID 925628Notes

Reaction equation

HRID 925628 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][CH:8]([O:11][C:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH:22]=[CH:21][C:20]([C:23](O)=[O:24])=[CH:19]4)=[CH:14][CH:13]=3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.Cl.CN(C)CCCN=[C:33]=[N:34][CH2:35][CH3:36].O.ON1C2C=CC=CC=2N=N1.N1CC1>CN(C)C=O.C(Cl)(Cl)Cl.O>[N:34]1([C:23]([C:20]2[CH:21]=[CH:22][N:18]([C:15]3[CH:14]=[CH:13][C:12]([O:11][CH:8]4[CH2:7][CH2:6][N:5]([CH:1]5[CH2:2][CH2:3][CH2:4]5)[CH2:10][CH2:9]4)=[CH:17][CH:16]=3)[CH:19]=2)=[O:24])[CH2:33][CH2:36][CH2:35]1

Participants

8

Reactant 4

HCID 9033AziridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 715990141-{4-[(1-cyclobutylpiperidin-4-yl)oxy]phenyl}-1H-pyrrole-3-carboxylic acid

Product 1

HCID 71599015azetidin-1-yl(1-{4-[(1-cyclobutylpiperidin-4-yl)oxy]phenyl}-1H-pyrrol-3-yl)methanoneYield 50.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 1-{4-[(1-cyclobutylpiperidin-4-yl)oxy]phenyl}-1H-pyrrole-3-carboxylic acid (0.1 g) synthesized in Example 2, 1-{3-(dimethylamino)propyl}-3-ethylcarbodiimide hydrochloride (0.085 g), 1-hydroxybenzotriazole hydrate (0.067 g) and aziridine (0.034 g) in N,N-dimethylformamide (0.1 ml) was stirred at room temperature for 16 hours. Water was added to the reaction mixture and extraction was conducted with chloroform. The organic layer was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (NH form silica gel; eluent: n-hexane/ethyl acetate=88/12-0/100) to give the titled compound as a colorless solid (0.056 g).

Workup

  1. concentrationThe organic layer was concentrated under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography (NH form silica gel; eluent: n-hexane/ethyl acetate=88/12-0/100)

Sources & evidence

ORD record
ord-5d8b65265af646478daa7ca17f90e174
Source dataset
uspto-grants-2016_03
Patent number
US09284324B2

Reaction notes

Loading…