1-Hydroxybenzotriazole → N-{1-[3-(3-ethoxy-4-methoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]propyl}2-(1-hydroxyethyl)-5-phenylpentanamide

HRID 1368310Notes

Reaction equation

HRID 1368310 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.C(N(C(C)C)C(C)C)C.Cl.CN(C)CCCN=C=NCC.[NH2:48][CH:49]([C:52]1[C:53](=[O:70])[NH:54][C:55]([CH2:58][C:59]2[CH:64]=[CH:63][C:62]([O:65][CH3:66])=[C:61]([O:67][CH2:68][CH3:69])[CH:60]=2)=[N:56][N:57]=1)[CH2:50][CH3:51]>>[CH2:68]([O:67][C:61]1[CH:60]=[C:59]([CH:64]=[CH:63][C:62]=1[O:65][CH3:66])[CH2:58][C:55]1[NH:54][C:53](=[O:70])[C:52]([CH:49]([NH:48][C:5](=[O:7])[CH:4]([CH:2]([OH:1])[CH3:3])[CH2:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:50][CH3:51])=[N:57][N:56]=1)[CH3:69]

Participants

6

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 183340382-(1-Hydroxyethyl)-5-phenylpentanoic acidHCID 1358247386-(1-aminopropyl)-3-(3-ethoxy-4-methoxybenzyl)-1,2,4-triazin-5(4H)-one

Product 1

HCID 135824728N-{1-[3-(3-ethoxy-4-methoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]propyl}2-(1-hydroxyethyl)-5-phenylpentanamide

Procedure

423 mg (1.90 mmol) of 2-(1-hydroxyethyl)-5-phenylpentanoic acid, are reacted analogously to Example 39A with 257 mg (1.90 mmol) of 1-hydroxy-1H-benzotriazole, 328 mg (2.54 mmol) of N-ethyldiisopropylamine, 365 mg (1.90 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride and 432 mg (1.27 mmol) of 6-(1-aminopropyl)-3-(3-ethoxy-4-methoxybenzyl)-1,2,4-triazin-5(4H)-one to give N-{1-[3-(3-ethoxy-4-methoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]propyl}2-(1-hydroxyethyl)-5-phenylpentanamide.

Sources & evidence

ORD record
ord-eabaaa206ad74814bb62e84c378a013e
Source dataset
uspto-grants-2003_06
Patent number
US06573263B2

Reaction notes

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