Dimethyl Sulfoxide → HCID 135824727, compound

HRID 1368305Notes

Reaction equation

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

Participants

Reactant 4

HCID 679Dimethyl Sulfoxide

HCID 8471Triethylamine

HCID 65578Oxalyl chloride

HCID 135824714HCID 135824714, compound

Product 1

HCID 135824727HCID 135824727, compound

Procedure

Analogously to Example 40A, 320 mg (2.50 mmol) of oxalyl chloride, 390 mg (5.00 mmol) of dimethyl sulphoxide, 800 mg (1.63 mmol) of (4E)-N-{1-[3-(3,4-dimethoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-2-(1-hydroxyethyl)-5-phenyl-4-pentenamide and 1.82 g (18.0 mmol) of triethylamine are reacted to give (4E)-2-acetyl-N-{1-[3-(3,4-dimethoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]-ethyl}-5-phenyl-4-pentenamide.

Sources & evidence

ORD record: ord-9094800b02b74bcfb45e63305a58090d
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06573263B2

Reaction notes

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