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Cesium carbonate → 4-[{2-[4-(6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl)-2-methoxyphenoxy]ethyl}(methyl)amino]benzonitrile

HRID 1181343
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HRID 1181343 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:16][C:15]3[C:14](=[O:17])[N:13]([C:18]4[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([O:25][CH3:26])[CH:19]=4)[CH:12]=[N:11][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.C1(C)C=CC(S(O[CH2:37][CH2:38][N:39]([CH3:48])[C:40]2[CH:45]=[CH:44][C:43]([C:46]#[N:47])=[CH:42][CH:41]=2)(=O)=O)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].O.C(O)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:16][C:15]3[C:14](=[O:17])[N:13]([C:18]4[CH:23]=[CH:22][C:21]([O:24][CH2:37][CH2:38][N:39]([CH3:48])[C:40]5[CH:45]=[CH:44][C:43]([C:46]#[N:47])=[CH:42][CH:41]=5)=[C:20]([O:25][CH3:26])[CH:19]=4)[CH:12]=[N:11][C:10]=3[CH:9]=2)=[CH:6][CH:7]=1
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참가 물질

6

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HCID 10796Cesium carbonateHCID 19096565Water ethanolHCID 589808956-(4-chlorophenyl)-3-(4-hydroxy-3-methoxyphenyl)thieno[3,2-d]pyrimidin-4(3H)-oneHCID 862220742-[4-Cyano(methyl)anilino]ethyl p-toluenesulfonate

생성물 1

HCID 589807804-[{2-[4-(6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl)-2-methoxyphenoxy]ethyl}(methyl)amino]benzonitrile
수율 98%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
75 °C

실험 절차

To a solution of 6-(4-chlorophenyl)-3-(4-hydroxy-3-methoxyphenyl)thieno[3,2-d]pyrimidin4(3H)-one (96 mg, 0.25 mmol, the preparation of which can be found in the section detailing the preparation of Example K1) in DMF was added 2-[4-cyano(methyl)anilino]ethyl p-toluenesulfonate (165 mg, 0.50 mmol) and cesium carbonate (0.24 g, 0.75 mmol) and the mixture was stirred with heating at 75° C. for 12 h. The reaction was allowed to cool and 10 mL solution of 20% water/ethanol was added. The resulting precipitate was filtered and dried in a vacuum oven to give the title compound (133 mg, 98%). 1H NMR (DMSO-D6) δ 3.10 (3H, s), 3.76 (3H, s), 3.87 (2H, t, J=3.7 Hz), 4.21 (2H, t, J=3.7 Hz), 6.87 (1H, d, J=7.3 Hz), 7.02-7.20 (3H, m), 7.58 (4H, m), 7.99 (3H, m), 8.38 (1H, s). LCMS m/z=543 (m+H+). Calcd. for C29H23ClN4O3S×1HCl: C, 60.11; H, 4.17; N; 9.67. Found: C, 59.78; H, 4.18; N, 9.44.

후처리

  1. temperatureto cool
  2. filtrationThe resulting precipitate was filtered
  3. customdried in a vacuum oven

출처 및 근거

ORD 기록
ord-4525461bec2c41bfa0d9995ab904cd75
출처 데이터셋
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07285557B2

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