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

HRID 1368306Notes

Reaction equation

HRID 1368306 reaction equation
ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC.[NH2:30][CH:31]([C:33]1[C:34](=[O:50])[NH:35][C:36]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[C:42]([O:48][CH3:49])[CH:41]=2)=[N:37][N:38]=1)[CH3:32].[C:51]([CH:54]([CH2:58][CH2:59][CH2:60][CH:61]1[CH2:66][CH2:65][CH2:64][CH2:63][CH2:62]1)[C:55](O)=[O:56])(=[O:53])[CH3:52]>>[C:51]([CH:54]([CH2:58][CH2:59][CH2:60][CH:61]1[CH2:62][CH2:63][CH2:64][CH2:65][CH2:66]1)[C:55]([NH:30][CH:31]([C:33]1[C:34](=[O:50])[NH:35][C:36]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[C:42]([O:48][CH3:49])[CH:41]=2)=[N:37][N:38]=1)[CH3:32])=[O:56])(=[O:53])[CH3:52]

Participants

6

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 183708122-Acetyl-5-cyclohexylpentanoic acid2×HCID 1356979236-(1-Aminoethyl)-3-[(3,4-dimethoxyphenyl)methyl]-1,2,4-triazin-5(2H)-one

Product 1

HCID 1360177642-acetyl-5-cyclohexyl-N-{1-[3-(3,4-dimethoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}pentanamide

Procedure

The amount of 2-acetyl-5-cyclohexylpentanoic acid in dichloromethane from Example 36A is reacted analogously to Example 39A with 280 mg (2.08 mmol) of 1-hydroxy-1H-benzotriazole, 610 mg (6.00 mmol) of 4-methylmorpholine, 400 mg (2.08 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride and 600 mg (2.08 mmol) of 6-(1-aminoethyl)-3-(3,4-dimethoxybenzyl)-1,2,4-triazin-5(4H)-one to give 2-acetyl-5-cyclohexyl-N-{1-[3-(3,4-dimethoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl }pentanamide.

Sources & evidence

ORD record
ord-ffa3ea4a8e0d43cf8aa8df1f12127ecd
Source dataset
uspto-grants-2003_06
Patent number
US06573263B2

Reaction notes

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