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

HRID 890711Notes

Reaction equation

HRID 890711 reaction equation
[OH:1][CH:2]([CH:4]([CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12])[C:5]([OH:7])=O)[CH3:3].ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC.[NH2:42][CH:43]([C:45]1[C:46](=[O:62])[NH:47][C:48]([CH2:51][C:52]2[CH:57]=[CH:56][C:55]([O:58][CH3:59])=[C:54]([O:60][CH3:61])[CH:53]=2)=[N:49][N:50]=1)[CH3:44]>>[CH3:61][O:60][C:54]1[CH:53]=[C:52]([CH:57]=[CH:56][C:55]=1[O:58][CH3:59])[CH2:51][C:48]1[NH:47][C:46](=[O:62])[C:45]([CH:43]([NH:42][C:5](=[O:7])[CH:4]([CH:2]([OH:1])[CH3:3])[CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12])[CH3:44])=[N:50][N:49]=1

Participants

6

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 108210762-(1-Hydroxyethyl)-6-heptenoic acidHCID 1356979236-(1-Aminoethyl)-3-[(3,4-dimethoxyphenyl)methyl]-1,2,4-triazin-5(2H)-one

Product 1

HCID 135697922N-{1-[3-(3,4-dimethoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-2-(1-hydroxyethyl)-6-heptenamide

Procedure

742 mg (4.31 mmol) of 2-(1-hydroxyethyl)-6-heptenoic acid (Example 22A) are reacted analogously to Example 23A with 580 mg (4.31 mmol) of 1-hydroxy-1H-benzotriazole, 870 mg (8.61 mmol) of 4-methylmorpholine, 830 mg (4.31 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride and 500 mg (1.72 mmol) of 6-(1-aminoethyl)-3-(3,4-dimethoxybenzyl)-1,2,4-triazin-5(4H)-one (Example 12A) to give N-{1-[3-(3,4-dimethoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-2-(1-hydroxyethyl)-6-heptenamide.

Sources & evidence

ORD record
ord-2672ab5f652e456c996c56d650297909
Source dataset
uspto-grants-2006_02
Patent number
US06998402B2

Reaction notes

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