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

HRID 1368304Notes

Reaction equation

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

Participants

Reactant 4

HCID 679Dimethyl Sulfoxide

HCID 8471Triethylamine

HCID 65578Oxalyl chloride

HCID 136017765N-(1-{3-[(3,4-Dimethoxyphenyl)methyl]-5-oxo-2,5-dihydro-1,2,4-triazin-6-yl}ethyl)-2-(1-hydroxyethyl)-5-phenylpentanamide

Product 1

HCID 1360177662-Acetyl-N-(1-{3-[(3,4-dimethoxyphenyl)methyl]-5-oxo-2,5-dihydro-1,2,4-triazin-6-yl}ethyl)-5-phenylpentanamide

Procedure

Analogously to Example 40A, 0.76 g (6.00 mmol) of oxalyl chloride, 1.01 g (12.9 mmol) of dimethyl sulphoxide, 1.95 g (3.93 mmol) of 2-(1-hydroxyethyl)-N-{1-[3-(3,4-dimethoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-5-phenyl-pentanamide and 4.36 g (43.1 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]ethyl}-5-phenylpentanamide.

Sources & evidence

ORD record: ord-7893b6f469e34a9bbd846031242cae46
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06573263B2

Reaction notes

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