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

HRID 1368300
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HRID 1368300 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([CH:14]([CH2:35][CH2:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:15]([NH:17][CH:18]([C:20]1[C:21](=[O:34])[NH:22][C:23]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)=[N:24][N:25]=1)[CH3:19])=[O:16])[CH3:13].C(N(CC)CC)C>ClCCl>[C:12]([CH:14]([CH2:35][CH2:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:15]([NH:17][CH:18]([C:20]1[C:21](=[O:34])[NH:22][C:23]([CH2:26][C:27]2[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=2)=[N:24][N:25]=1)[CH3:19])=[O:16])(=[O:11])[CH3:13]
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참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1358247302-(1-hydroxyethyl)-N-{1-[3-(4-methylbenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-5-phenylpentanamide

생성물 1

HCID 1358247172-Acetyl-N-{1-[3-(4-methylbenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-5-phenylpentanamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-70 °C

실험 절차

270 mg (2.14 mmol) of oxalyl chloride in 10 ml of dichloromethane are treated dropwise at −70° C. with 360 mg (4.64 mmol) of dimethyl sulphoxide. The mixture is stirred at −70° C. for 30 min, then 800 mg (1.78 mmol) of 2-(1-hydroxyethyl)-N-{1-[3-(4-methylbenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-5-phenylpentanamide are added. After a further 30 min, during which the temperature in the batch rises to about −60° C., 900 mg (8.92 mmol) of triethylamine are added and the cooling bath is then removed. If the batch temperature has warmed almost to room temperature, 10 ml of water are added and, after stirring briefly, the phases are separated. The dried organic phase is chromatographed in dichloromethane/methanol 50/1.

후처리

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

출처 및 근거

ORD 기록
ord-d5acf0eceffe42a29c487951eba8d915
출처 데이터셋
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06573263B2

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