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

HRID 1260236ノート

反応式

HRID 1260236 の反応式
[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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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-isopropyl-benzensulfonylchloride (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.

後処理

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

出典と根拠

ORDレコード
ord-8f99cf9fff5442c8ba1b821246b36df5
出典データセット
uspto-grants-2013_06
特許番号
US08470810B2

反応ノート

読み込み中…