Dimethyl Sulfoxide → 2-Acetyl-N-{1-[3-(3,4-dimethoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]-ethyl}-6-heptenamide

HRID 890712ノート

反応式

HRID 890712 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:38]=[CH:39][C:40]=1[O:41][CH3:42])[CH2:16][C:17]1[NH:22][C:21](=[O:23])[C:20]([CH:24]([NH:26][C:27](=[O:37])[CH:28]([CH:34]([OH:36])[CH3:35])[CH2:29][CH2:30][CH2:31][CH:32]=[CH2:33])[CH3:25])=[N:19][N:18]=1.C(N(CC)CC)C>ClCCl>[C:34]([CH:28]([CH2:29][CH2:30][CH2:31][CH:32]=[CH2:33])[C:27]([NH:26][CH:24]([C:20]1[C:21](=[O:23])[NH:22][C:17]([CH2:16][C:15]2[CH:38]=[CH:39][C:40]([O:41][CH3:42])=[C:13]([O:12][CH3:11])[CH:14]=2)=[N:18][N:19]=1)[CH3:25])=[O:37])(=[O:36])[CH3:35]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 135697922N-{1-[3-(3,4-dimethoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-2-(1-hydroxyethyl)-6-heptenamide

生成物 1

HCID 1356979142-Acetyl-N-{1-[3-(3,4-dimethoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]-ethyl}-6-heptenamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-70 °C

実験手順

100 mg (0.76 mmol) of oxalyl chloride in 5 ml of dichloromethane are treated dropwise at −70° C. with 130 mg (1.64 mmol) of dimethyl sulphoxide. The mixture is stirred at −70° C. for 30 min, then 280 mg (0.63 mmol) of N-{1-[3-(3,4-dimethoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-2-(1-hydroxyethyl)-6-heptenamide (Example 29A) are added. After a further 30 min, during which the temperature in the batch rises to about −60° C., 320 mg (3.15 mmol) of triethylamine are added and the cooling bath is then removed. If the batch temperature is warmed almost to room temperature, 10 ml of water are added and the phases are separated after stirring briefly. The dried organic phase is chromatographed in dichloromethane/methanol 50/1.

後処理

  1. waitAfter a further 30 min
  2. customrises to about −60° C.
  3. customthe cooling bath is then removed
  4. temperatureIf the batch temperature is warmed almost to room temperature
  5. addition10 ml of water are added
  6. customthe phases are separated
  7. stirringafter stirring briefly
  8. customThe dried organic phase is chromatographed in dichloromethane/methanol 50/1

出典と根拠

ORDレコード
ord-b067f4a5823f41d1b226fdbd570f6f94
出典データセット
uspto-grants-2006_02
特許番号
US06998402B2

反応ノート

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