Dimethylformamide → 4-i-Propyl-phenyl sulfamic acid-[6-[2-(pyrimidin-2-yloxy)ethoxy]-5-(o-methoxyphenoxy)-2-(4-pyridyl)pyrimidin-4-yl]-amide

HRID 10251

反応式

HRID 10251 の反応式
[OH:1][CH2:2][CH2:3][O:4][C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[N:8]=[C:7]([NH:17][S:18](=[O:30])(=[O:29])[NH:19][C:20]2[CH:25]=[CH:24][C:23]([CH:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=2)[C:6]=1[O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[O:38][CH3:39].[H-].[Na+].Cl[C:43]1[N:48]=[CH:47][CH:46]=[CH:45][N:44]=1.CN(C=O)C>C1COCC1>[N:44]1[CH:45]=[CH:46][CH:47]=[N:48][C:43]=1[O:1][CH2:2][CH2:3][O:4][C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[N:8]=[C:7]([NH:17][S:18](=[O:30])(=[O:29])[NH:19][C:20]2[CH:21]=[CH:22][C:23]([CH:26]([CH3:28])[CH3:27])=[CH:24][CH:25]=2)[C:6]=1[O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[O:38][CH3:39]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 744042-ChloropyrimidineHCID 103028114-i-Propyl-phenyl sulfamic acid-[6-(2-hydroxy-ethoxy)-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidin-4-yl]-amide

生成物 1

HCID 102827614-i-Propyl-phenyl sulfamic acid-[6-[2-(pyrimidin-2-yloxy)ethoxy]-5-(o-methoxyphenoxy)-2-(4-pyridyl)pyrimidin-4-yl]-amide収率 73%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

4-i-Propyl-phenyl sulfamic acid-[6-(2-hydroxy-ethoxy)-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidin-4-yl]-amide (60 mg, Example 3) was dissolved in THF (8 ml) and sodium hydride (14 mg, 60% dispersion in mineral oil) was added and stirring continued for 10 min. 2-Chloro-pyrimidine (22 mg) was added and the mixture was heated to 60° C. for 90 min. DMF (0.5 ml) was added and the solution was stirred at r.t. for 48 h. The solvents were evaporated, water (12 ml) and a 10/solution of citric acid was added until the pH was 3. The precipitate was filtered off and washed with water and purified by recrystallization from diethyl ether to give 4-i-propyl-phenyl sulfamic acid-[6-[2-(pyrimidin-2-yloxy)-ethoxy]-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidin-4-yl]-amide (50 mg). tR=4.80 min, (LC); [M+H]+=630.91 (ES+).

後処理

  1. stirringthe solution was stirred at r.t. for 48 h
  2. customThe solvents were evaporated
  3. additionwater (12 ml) and a 10/solution of citric acid was added until the pH was 3
  4. filtrationThe precipitate was filtered off
  5. washwashed with water
  6. custompurified by recrystallization from diethyl ether

出典と根拠

ORDレコード
ord-fd75d1250ff34f74a530d064642bf2d5
出典データセット
uspto-grants-2006_08
特許番号
US07094781B2

関連ノート

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