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

HRID 925628노트

반응식

HRID 925628 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6212Chloroform용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-5d8b65265af646478daa7ca17f90e174
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284324B2

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