4-Methylmorpholine → 2-acetyl-N-{1-[3-(4-methoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}octanamide

HRID 890709Notes

Reaction equation

HRID 890709 reaction equation
[C:1]([CH:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:5]([O:7]C)=O)(=[O:3])[CH3:2].C(C(CCCCCC)C(O)=O)(=O)C.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC.[NH2:57][CH:58]([C:60]1[C:61](=[O:75])[NH:62][C:63]([CH2:66][C:67]2[CH:72]=[CH:71][C:70]([O:73][CH3:74])=[CH:69][CH:68]=2)=[N:64][N:65]=1)[CH3:59]>ClCCl>[C:1]([CH:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:5]([NH:57][CH:58]([C:60]1[C:61](=[O:75])[NH:62][C:63]([CH2:66][C:67]2[CH:72]=[CH:71][C:70]([O:73][CH3:74])=[CH:69][CH:68]=2)=[N:64][N:65]=1)[CH3:59])=[O:7])(=[O:3])[CH3:2]

Participants

8

Reactant 6

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3390996Methyl 2-acetyloctanoateHCID 187645892-Acetyloctanoic acidHCID 1356979216-(1-aminoethyl)-3-(4-methoxybenzyl)-1,2,4-triazin-5(4H)-one

Product 1

HCID 1356979172-acetyl-N-{1-[3-(4-methoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}octanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.18 g (5.91 mmol) of methyl 2-acetyloctanoate (Example 18A) are hydrolysed to 2-acetyloctanoic acid according to Example 19A. The acid in 20 ml of dichloromethane is reacted analogously to Example 23A with 800 mg (5.90 mmol) of 1-hydroxy-1H-benzotriazole, 1.66 g (16.4 mmol) of 4-methylmorpholine, 1.13 g (5.9 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride and 900 mg (3.5 mmol) of 6-(1-aminoethyl)-3-(4-methoxybenzyl)-1,2,4-triazin-5(4H)-one (Example 10A) to give 2-acetyl-N-{1-[3-(4-methoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}octanamide.

Sources & evidence

ORD record
ord-fd4660dd86e04fc8bbbd2052178d3b9a
Source dataset
uspto-grants-2006_02
Patent number
US06998402B2

Reaction notes

Loading…