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Potassium Carbonate → HCID 57898124, 화합물

HRID 1693546
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HRID 1693546 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=O)[C:10]2[CH:15]=[CH:14][C:13]([CH:16]([CH3:18])[CH3:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C([O:22][C:23]([C:25]1[C:29]([NH2:30])=[C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:27][N:26]=1)=O)C.C([O-])([O-])=O.[K+].[K+]>S(Cl)(Cl)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:23](=[O:22])[C:25]3=[N:26][O:27][C:28]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)=[C:29]3[N:30]=[C:9]2[C:10]2[CH:15]=[CH:14][C:13]([CH:16]([CH3:18])[CH3:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1
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5

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HCID 11430Potassium CarbonateHCID 1406457HCID 1406457, 화합물HCID 57897974HCID 57897974, 화합물

생성물 1

HCID 57898124HCID 57898124, 화합물

시약·촉매·용매 1

HCID 24386Thionyl Chloride용매2회

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온도
180 °C

실험 절차

A suspension of N-(4-chloro-phenyl)-4-isopropyl-benzamide (20.0 mg, 0.073 mmol) in thionyl chloride (0.5 mL) is heated at 80° C. for 1.5 h before thionyl chloride is removed in vacuo. The reaction residue is then taken in anhydrous acetonitrile (1.5 mL), followed by the addition of 4-amino-5-phenyl-isoxazole-3-carboxylic acid ethyl ester from step B (18.7 mg, 0.081 mmol) and anhydrous K2CO3 (25.2 mg, 0.182 mmol). The reaction mixture is heated under nitrogen atmosphere at 180° C. in a microwave for 2 h, then cooled down to room temperature. K2CO3 is removed by filtration. The filtrate is concentrated and purified by preparative LC/MS to provide the title compound; 1H NMR (CDCl3, 400 MHz) δ 8.37 (dd, 2H), 7.53 (m, 3H), 7.31 (d, 2H), 7.25 (d, 2H), 7.11 (m, 4H), 2.87 (m, 1H), 1.22 (s, 3H), 1.20 (s, 3H); HPLC-MS calculated for C26H20ClN3O2 (M+H+) 442.1. Found: 442.2.

후처리

  1. customis removed in vacuo
  2. temperaturecooled down to room temperature
  3. customK2CO3 is removed by filtration
  4. concentrationThe filtrate is concentrated
  5. custompurified by preparative LC/MS

출처 및 근거

ORD 기록
ord-7cafd5da932946c78501e37ecd3707aa
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08158634B2

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