Dimethyl Sulfoxide → 2-(4-Fluorobenzyl)-8-methyl-10-methoxy-1,9-dioxo-1,2,6,7,8,9-hexahydropyrazino[1',2':1,5]pyrrolo[2,3-d]pyridazine-4-carboxaldehyde

HRID 494129ノート

反応式

HRID 494129 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]1[CH:38]=[CH:37][C:15]([CH2:16][N:17]2[C:22](=[O:23])[C:21]3[C:24]([O:33][CH3:34])=[C:25]4[C:30](=[O:31])[N:29]([CH3:32])[CH2:28][CH2:27][N:26]4[C:20]=3[C:19]([CH2:35][OH:36])=[N:18]2)=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl.O>[F:11][C:12]1[CH:38]=[CH:37][C:15]([CH2:16][N:17]2[C:22](=[O:23])[C:21]3[C:24]([O:33][CH3:34])=[C:25]4[C:30](=[O:31])[N:29]([CH3:32])[CH2:28][CH2:27][N:26]4[C:20]=3[C:19]([CH:35]=[O:36])=[N:18]2)=[CH:14][CH:13]=1

参加物

7

反応物 4

HCID 679Dimethyl Sulfoxide2 回HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 688646802-(4-fluorobenzyl)-4-(hydroxymethyl)-10-methoxy-8-methyl-7,8-dihydropyrazino[1',2':1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione

生成物 1

HCID 866248002-(4-Fluorobenzyl)-8-methyl-10-methoxy-1,9-dioxo-1,2,6,7,8,9-hexahydropyrazino[1',2':1,5]pyrrolo[2,3-d]pyridazine-4-carboxaldehyde

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒4 回

反応条件

温度
-35 °C

実験手順

To a cold (−78° C.) solution of oxalyl chloride (0.25 mL, 2.8 mmol) in anhydrous dichloromethane (15 mL) under an atmosphere of nitrogen, a solution of anhydrous DMSO (0.21 mL, 2.93 mmol) in anhydrous dichloromethane (5 mL) was added. The resultant mixture was stirred at the same temperature for 10 minutes. A solution of 2-(4-fluorobenzyl)-4-(hydroxymethyl)-10-methoxy-8-methyl-7,8-dihydropyrazino[1′,2′:1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione (0.47 g, 1.22 mmol) in a mixture of anhydrous dichloromethane (3 mL) and DMSO (5 mL) was added. After stirring at the same temperature for 2 hours, the reaction mixture was allowed to warm to −35° C., and treated with triethylamine (8 mL). The reaction mixture was allowed to warm to room temperature and pour into water (40 mL). The product mixture was diluted with dichloromethane. The organic extract was dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residual oil was treated with hexane and cooled to 0° C. The solid precipitated was filtered and vacuum dried to provide the title compound.

後処理

  1. additionwas added
  2. temperatureto warm to room temperature
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. additionThe residual oil was treated with hexane
  8. temperaturecooled to 0° C
  9. customThe solid precipitated
  10. filtrationwas filtered
  11. customvacuum dried

出典と根拠

ORDレコード
ord-8800c2e40e834a35927902fcb4c27c9f
出典データセット
uspto-grants-2009_05
特許番号
US07538112B2

反応ノート

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