Morpholine → 5-(5-(6-(Trifluoromethyl)quinolin-4-yloxy)pentyloxy)-2-(morpholinomethyl)-4H-pyran-4-one

HRID 2108862ノート

反応式

HRID 2108862 の反応式
CS(O[CH2:6][C:7]1[O:8][CH:9]=[C:10]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]([C:31]([F:34])([F:33])[F:32])[CH:29]=3)[N:24]=[CH:23][CH:22]=2)[C:11](=[O:13])[CH:12]=1)(=O)=O.[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>ClCCl>[F:33][C:31]([F:34])([F:32])[C:28]1[CH:29]=[C:30]2[C:25](=[CH:26][CH:27]=1)[N:24]=[CH:23][CH:22]=[C:21]2[O:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][O:14][C:10]1[C:11](=[O:13])[CH:12]=[C:7]([CH2:6][N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)[O:8][CH:9]=1

参加物

4

反応物 2

HCID 8083MorpholineHCID 57629435HCID 57629435、化合物

生成物 1

HCID 103683885-(5-(6-(Trifluoromethyl)quinolin-4-yloxy)pentyloxy)-2-(morpholinomethyl)-4H-pyran-4-one収率 35%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
45 °C

実験手順

Methanesulfonic acid 4-oxo-5-[5-(7-trifluoromethyl-quinolin-4-yloxy)-pentyloxy]-4H-pyran-2-ylmethyl ester 16 (100 mg, 0.20 mmol) was dissolved in dichloromethane (5 mL). Morpholine (44 μL, 0.50 mmol) was added via syringe. The mixture was stirred at 45° C. for 18 h. After cooling to room temperature CH2Cl2 (75 ml) was added and the mixture was washed with NaHCO3 10% (3×50 mL) and brine (3×50 mL). The organic layer was dried over MgSO4, filtered and evaporated. The crude product was purified by column chromatography on silica using as eluent CH2Cl2:MeOH=9:1. 5-(5-(6-(Trifluoromethyl)quinolin-4-yloxy)pentyloxy)-2-(morpholinomethyl)-4H-pyran-4-one EHT 1426 was obtained (37 mg, 35% yield) as an orange oil.

後処理

  1. additionwas added
  2. washthe mixture was washed with NaHCO3 10% (3×50 mL) and brine (3×50 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by column chromatography on silica using as eluent CH2Cl2

出典と根拠

ORDレコード
ord-edd3bcdce3a744bba2dda03acdb7cc9b
出典データセット
uspto-grants-2009_04
特許番号
US07514432B2

反応ノート

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