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

HRID 1368311Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:13][C:14]1[CH:15]=[C:16]([CH:44]=[CH:45][C:46]=1[O:47][CH3:48])[CH2:17][C:18]1[NH:23][C:22](=[O:24])[C:21]([CH:25]([NH:28][C:29](=[O:43])[CH:30]([CH:40]([OH:42])[CH3:41])[CH2:31][CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:26][CH3:27])=[N:20][N:19]=1)[CH3:12].C(N(C(C)C)C(C)C)C>>[C:40]([CH:30]([CH2:31][CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:29]([NH:28][CH:25]([C:21]1[C:22](=[O:24])[NH:23][C:18]([CH2:17][C:16]2[CH:44]=[CH:45][C:46]([O:47][CH3:48])=[C:14]([O:13][CH2:11][CH3:12])[CH:15]=2)=[N:19][N:20]=1)[CH2:26][CH3:27])=[O:43])(=[O:42])[CH3:41]

Participants

Reactant 4

HCID 679Dimethyl Sulfoxide

HCID 65578Oxalyl chloride

HCID 81531Diisopropylethylamine

HCID 135824728N-{1-[3-(3-ethoxy-4-methoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]propyl}2-(1-hydroxyethyl)-5-phenylpentanamide

Product 1

HCID 1363602552-acetyl-N-{1-[3-(3-ethoxy-4-methoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]propyl}-5-phenylpentanamide

Procedure

Analogously to Example 40A, 12.9 mg (0.10 mmol) of oxalyl chloride, 9.91 mg (0.13 mmol) of dimethyl sulphoxide, 43.0 mg (0.08 mmol) of N-{1-[3-(3-ethoxy-4-methoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]propyl}2-(1-hydroxyethyl)-5-phenylpentanamide and 32.8 mg (0.25 mmol) of N-ethyldiisopropylamine are reacted to give 2-acetyl-N-{1-[3-(3-ethoxy-4-methoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]propyl}-5-phenylpentanamide.

Sources & evidence

ORD record: ord-ab8df984a40f44218807cba8835ba1a8
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06573263B2

Reaction notes

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