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

HRID 1368313Notes

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[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=[CH:29][CH:28]=2)=[N:24][N:25]=1)[CH3:19])=[O:16])[CH3:13].C(N(C(C)C)C(C)C)C>>[C:12]([CH:14]([CH2:38][CH2:39][CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[C:15]([NH:17][CH:18]([C:20]1[C:21](=[O:37])[NH:22][C:23]([CH2:26][C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=[CH:29][CH:28]=2)=[N:24][N:25]=1)[CH3:19])=[O:16])(=[O:11])[CH3:13]

Participants

Reactant 4

HCID 679Dimethyl Sulfoxide

HCID 65578Oxalyl chloride

HCID 81531Diisopropylethylamine

HCID 1358247242-(1-hydroxyethyl)-N-{1-[3-(1-naphthylmethyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-5-phenylpentanamide

Product 1

HCID 1358247162-acetyl-N-{1-[3-(1-naphthylmethyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-5-phenylpentanamide

Procedure

Analogously to Example 40, 310 mg (2.44 mmol) of oxalyl chloride, 239 mg (3.05 mmol) of dimethyl sulphoxide, 740 mg (1.53 mmol) of 2-(1-hydroxyethyl)-N-{1-[3-(1-naphthylmethyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-5-phenyl-pentanamide and 790 mg (6.11 mmol) of N-ethyldiisopropylamine are reacted to give 2-acetyl-N-{1-[3-(1-naphthylmethyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-5-phenylpentanamide.

Sources & evidence

ORD record: ord-a93c1b15dcf24ddf8f0c5bf753822b25
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06573263B2

Reaction notes

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