Pyridine → N-[4-(3-cyano-1-cyclobutyl-6-ethoxy-indol-2-yl)phenyl]morpholine-4-carboxamide

HRID 252604

反応式

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:22]3[CH2:25][CH2:24][CH2:23]3)[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH2:20][CH3:21])[CH:11]=3)=[CH:4][CH:3]=1.Cl[C:27](OC1C=CC([N+]([O-])=O)=CC=1)=[O:28].N1C=CC=CC=1.[NH:45]1[CH2:50][CH2:49][O:48][CH2:47][CH2:46]1>C(Cl)Cl>[C:17]([C:16]1[C:15]2[C:10](=[CH:11][C:12]([O:19][CH2:20][CH3:21])=[CH:13][CH:14]=2)[N:9]([CH:22]2[CH2:23][CH2:24][CH2:25]2)[C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:27]([N:45]2[CH2:50][CH2:49][O:48][CH2:47][CH2:46]2)=[O:28])=[CH:7][CH:6]=1)#[N:18]

参加物

実験手順

2-(4-aminophenyl)-1-cyclobutyl-6-ethoxy-1H-indole-3-carbonitrile (40 mg, 0.12 mmol), 4-nitrophenyl chloroformate (60 mg, 0.30 mmol), CH2Cl2 (400 μL), and pyridine (25 μL, 0.31 mmol) are stirred at room temperature for 1 hour. Morpholine (60 μL, 0.70 mmol) is added. After stirring at room temperature for an additional 30 minutes, the reaction mixture is diluted in CH2Cl2 and is washed with dilute aqueous NaOH to remove the yellow nitrophenol byproduct. The organic layer is dried and concentrated. Purification by silica gel chromatography (CH2Cl2/EtOAc, 7/3) yields morpholine-4-carboxylic acid [4-(3-cyano-1-cyclobutyl-6-ethoxy-1H-indol-2-yl)-phenyl]-amide (53 mg, 100%) as a white solid.

後処理

washis washed with dilute aqueous NaOH
customto remove the yellow nitrophenol byproduct
customThe organic layer is dried
concentrationconcentrated
customPurification by silica gel chromatography (CH2Cl2/EtOAc, 7/3)

出典と根拠

ORDレコード: ord-c93187913ef345a497e3afb8e28d734d
出典データセット: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07868037B2

反応式

参加物

反応物 4

生成物 1

試薬・触媒・溶媒 1

実験手順

後処理

出典と根拠

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