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

HRID 890708Notes

Reaction equation

HRID 890708 reaction equation
[C:1]([CH:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:5]([O:7]C)=O)(=[O:3])[CH3:2].C(C(CCCCC)C(O)=O)(=O)C.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC.[NH2:55][CH:56]([C:58]1[C:59](=[O:73])[NH:60][C:61]([CH2:64][C:65]2[CH:70]=[CH:69][C:68]([O:71][CH3:72])=[CH:67][CH:66]=2)=[N:62][N:63]=1)[CH3:57]>ClCCl>[C:1]([CH:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:5]([NH:55][CH:56]([C:58]1[C:59](=[O:73])[NH:60][C:61]([CH2:64][C:65]2[CH:70]=[CH:69][C:68]([O:71][CH3:72])=[CH:67][CH:66]=2)=[N:62][N:63]=1)[CH3:57])=[O:7])(=[O:3])[CH3:2]

Participants

8

Reactant 6

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10511765Methyl 2-acetylheptanoateHCID 149151282-Acetylheptanoic acidHCID 1356979216-(1-aminoethyl)-3-(4-methoxybenzyl)-1,2,4-triazin-5(4H)-one

Product 1

HCID 1356979202-acetyl-N-{1-[3-(4-methoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}heptanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.29 g (6.91 mmol) of methyl 2-acetylheptanoate (Example 16A) are hydrolysed to 2-acetylheptanoic acid according to Example 17A. The acid in 20 ml of dichloromethane is reacted analogously to Example 23A with 903 mg (6.90 mmol) of 1-hydroxy-1H-benzotriazole, 2.02 g (20 mmol) of 4-methylmorpholine, 1.32 g (6.90 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride and 890 mg (3.4 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}heptanamide.

Sources & evidence

ORD record
ord-318538e20c9f4d6ba1025f605cc326be
Source dataset
uspto-grants-2006_02
Patent number
US06998402B2

Reaction notes

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