Dimethyl Sulfoxide → 2-acetyl-N-{1-[3-(3,4-dimethoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]propyl}-5-phenylpentanamide

HRID 1368309Notes

Reaction equation

HRID 1368309 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:43]=[CH:44][C:45]=1[O:46][CH3:47])[CH2:16][C:17]1[NH:22][C:21](=[O:23])[C:20]([CH:24]([NH:27][C:28](=[O:42])[CH:29]([CH:39]([OH:41])[CH3:40])[CH2:30][CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:25][CH3:26])=[N:19][N:18]=1.C(N(CC)CC)C>>[C:39]([CH:29]([CH2:30][CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:28]([NH:27][CH:24]([C:20]1[C:21](=[O:23])[NH:22][C:17]([CH2:16][C:15]2[CH:43]=[CH:44][C:45]([O:46][CH3:47])=[C:13]([O:12][CH3:11])[CH:14]=2)=[N:18][N:19]=1)[CH2:25][CH3:26])=[O:42])(=[O:41])[CH3:40]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 135824723HCID 135824723, compound

Product 1

HCID 1358247312-acetyl-N-{1-[3-(3,4-dimethoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]propyl}-5-phenylpentanamide

Procedure

Analogously to Example 40A, 440 mg (305 mmol) of oxalyl chloride, 550 mg (7.00 mmol) of dimethyl sulphoxide, 920 mg (1.82 mmol) of N-{1-[3-(3,4-dimethoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]propyl}-2-(1-hydroxyethyl)-5-phenyl-pentanamide and 1.82 g (18 mmol) of triethylamine are reacted to give 2-acetyl-N-{1-[3-(3,4-dimethoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]propyl}-5-phenylpentanamide.

Sources & evidence

ORD record
ord-c07f8c58abec4cad92d297d8f952631b
Source dataset
uspto-grants-2003_06
Patent number
US06573263B2

Reaction notes

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