Dimethyl Sulfoxide → 2-acetyl-N-{1-[3-(4-methoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-5-phenyl-pentanamide

HRID 1368302Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([CH:14]([CH2:36][CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:15]([NH:17][CH:18]([C:20]1[C:21](=[O:35])[NH:22][C:23]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)=[N:24][N:25]=1)[CH3:19])=[O:16])[CH3:13].C(N(CC)CC)C>>[C:12]([CH:14]([CH2:36][CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:15]([NH:17][CH:18]([C:20]1[C:21](=[O:35])[NH:22][C:23]([CH2:26][C:27]2[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=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 1358247202-(1-hydroxyethyl)-N-{1-[3-(4-methoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-5-phenylpentanamide

Product 1

HCID 1354095962-acetyl-N-{1-[3-(4-methoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-5-phenyl-pentanamide

Procedure

Analogously to Example 40A, 250 mg (1.94 mmol) of oxalyl chloride, 330 mg (4.2 mmol) of dimethyl sulphoxide, 750 mg (1.61 mmol) of 2-(1-hydroxyethyl)-N-{1-[3-(4-methoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-5-phenyl-pentanamide and 820 mg (8.07 mmol) of triethylamine are reacted to give 2-acetyl-N-{1-[3-(4-methoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-5-phenyl-pentanamide.

Sources & evidence

ORD record: ord-2ddb50f12a9c408ea6aefce84222e8eb
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06573263B2

Reaction notes

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