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

HRID 252604

반응식

HRID 252604 반응식
[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]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 8083MorpholineHCID 821294-Nitrophenyl chloroformateHCID 250520112-(4-Aminophenyl)-1-cyclobutyl-6-ethoxy-indole-3-carbonitrile

생성물 1

HCID 49772271N-[4-(3-cyano-1-cyclobutyl-6-ethoxy-indol-2-yl)phenyl]morpholine-4-carboxamide수율 100%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-c93187913ef345a497e3afb8e28d734d
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868037B2

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