Pyridine → 4-Isopropyl-N-[4-(1-propionyl-azetidin-3-yl)-phenyl]-benzenesulfonamide

HRID 2262621노트

반응식

HRID 2262621 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:13][N:12]([C:14](=[O:17])[CH2:15][CH3:16])[CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.O.O.Cl[Sn]Cl.NC1C=CC=CC=1.N1C=CC=CC=1.[CH:36]([C:39]1[CH:44]=[CH:43][C:42]([S:45](Cl)(=[O:47])=[O:46])=[CH:41][CH:40]=1)([CH3:38])[CH3:37]>CCO.C(Cl)Cl>[CH:36]([C:39]1[CH:44]=[CH:43][C:42]([S:45]([NH:1][C:4]2[CH:9]=[CH:8][C:7]([CH:10]3[CH2:13][N:12]([C:14](=[O:17])[CH2:15][CH3:16])[CH2:11]3)=[CH:6][CH:5]=2)(=[O:47])=[O:46])=[CH:41][CH:40]=1)([CH3:38])[CH3:37]

참가 물질

8

반응물 5

HCID 1049PyridineHCID 6115AnilineHCID 61436Stannous chloride dihydrateHCID 27348824-(Propan-2-yl)benzene-1-sulfonyl chlorideHCID 574700801-(3-(4-Nitrophenyl)azetidin-1-yl)propan-1-one

생성물 1

HCID 536286634-Isopropyl-N-[4-(1-propionyl-azetidin-3-yl)-phenyl]-benzenesulfonamide수율 36%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6344Dichloromethane용매

실험 절차

Following the same procedure as described in 46.5, 1-[3-(4-nitro-phenyl)-azetidin-1-yl]-propan-1-one (480 mg, 2.04 mmol) in EtOH (20 ml) was treated with SnCl2.2H2O (2.25 g, 9.97 mmol) and half of the resulting aniline in CH2Cl2 (15 ml) was then treated with pyridine (140 μl, 1.71 mmol) and 4-isopropylbenzensulfonylchloride (230 μl, 1.28 mmol). Purification of the crude product by flash column chromatography (heptane:ethyl acetate, 1:1) provided the title compound (140 mg, 36% for two steps) as a pale yellow gum.

후처리

  1. customPurification of the crude product by flash column chromatography (heptane:ethyl acetate, 1:1)

출처 및 근거

ORD 기록
ord-8f37ce5682c74dc594d38aa395d54d0d
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07851463B2

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