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

HRID 1368303Notes

Reaction equation

HRID 1368303 reaction equation
[OH:1][CH:2]([CH:4]([CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]([OH:7])=O)[CH3:3].ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC.[NH2:46][CH:47]([C:49]1[C:50](=[O:66])[NH:51][C:52]([CH2:55][C:56]2[CH:61]=[CH:60][C:59]([O:62][CH3:63])=[C:58]([O:64][CH3:65])[CH:57]=2)=[N:53][N:54]=1)[CH3:48]>>[OH:1][CH:2]([CH:4]([CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]([NH:46][CH:47]([C:49]1[C:50](=[O:66])[NH:51][C:52]([CH2:55][C:56]2[CH:61]=[CH:60][C:59]([O:62][CH3:63])=[C:58]([O:64][CH3:65])[CH:57]=2)=[N:53][N:54]=1)[CH3:48])=[O:7])[CH3:3]

Participants

6

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 183340382-(1-Hydroxyethyl)-5-phenylpentanoic acidHCID 1356979236-(1-Aminoethyl)-3-[(3,4-dimethoxyphenyl)methyl]-1,2,4-triazin-5(2H)-one

Product 1

HCID 136017765N-(1-{3-[(3,4-Dimethoxyphenyl)methyl]-5-oxo-2,5-dihydro-1,2,4-triazin-6-yl}ethyl)-2-(1-hydroxyethyl)-5-phenylpentanamide

Procedure

1.01 g (4.55 mmol) of 2-(1-hydroxyethyl)-5-phenylpentanoic acid are reacted analogously to Example 39A with 0.67 g (4.96 mmol) of 1-hydroxy-1H-benzotriazole, 1.05 g (10.3 mmol) of 4-methylmorpholine, 0.95 g (4.96 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride and 1.20 g (4.13 mmol) of 6-(1-aminoethyl)-3-(3,4-dimethoxybenzyl)-1,2,4-triazin-5(4H)-one to give 2-(1-hydroxyethyl)-N-{1-[3-(3,4-dimethoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-tri azin-6-yl]-ethyl)}5-phenylpentanamide.

Workup

  1. customto give 2-(1-hydroxyethyl)-N-{1-[3-(3,4-dimethoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-tri azin-6-yl]-ethyl)}5-phenylpentanamide

Sources & evidence

ORD record
ord-24b13a29852f44d29a9b7a382daf9f7c
Source dataset
uspto-grants-2003_06
Patent number
US06573263B2

Reaction notes

Loading…