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

HRID 890712Notes

Reaction equation

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

Participants

Conditions

Temperature: -70 °C

Procedure

100 mg (0.76 mmol) of oxalyl chloride in 5 ml of dichloromethane are treated dropwise at −70° C. with 130 mg (1.64 mmol) of dimethyl sulphoxide. The mixture is stirred at −70° C. for 30 min, then 280 mg (0.63 mmol) of N-{1-[3-(3,4-dimethoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-2-(1-hydroxyethyl)-6-heptenamide (Example 29A) are added. After a further 30 min, during which the temperature in the batch rises to about −60° C., 320 mg (3.15 mmol) of triethylamine are added and the cooling bath is then removed. If the batch temperature is warmed almost to room temperature, 10 ml of water are added and the phases are separated after stirring briefly. The dried organic phase is chromatographed in dichloromethane/methanol 50/1.

Workup

waitAfter a further 30 min
customrises to about −60° C.
customthe cooling bath is then removed
temperatureIf the batch temperature is warmed almost to room temperature
addition10 ml of water are added
customthe phases are separated
stirringafter stirring briefly
customThe dried organic phase is chromatographed in dichloromethane/methanol 50/1

Sources & evidence

ORD record: ord-b067f4a5823f41d1b226fdbd570f6f94
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06998402B2

Reaction notes

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