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

HRID 1368312Notes

Reaction equation

HRID 1368312 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:51]1[C:52](=[O:68])[NH:53][C:54]([CH2:57][C:58]2[C:67]3[C:62](=[CH:63][CH:64]=[CH:65][CH:66]=3)[CH:61]=[CH:60][CH:59]=2)=[N:55][N:56]=1)[CH3:50]>>[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:48][CH:49]([C:51]1[C:52](=[O:68])[NH:53][C:54]([CH2:57][C:58]2[C:67]3[C:62](=[CH:63][CH:64]=[CH:65][CH:66]=3)[CH:61]=[CH:60][CH:59]=2)=[N:55][N:56]=1)[CH3:50])=[O:7])[CH3:3]

Participants

6

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 183340382-(1-Hydroxyethyl)-5-phenylpentanoic acidHCID 1358247226-(1-aminoethyl)-3-(1-naphthylmethyl)-1,2,4-triazin-5(4H)-one

Product 1

HCID 1358247242-(1-hydroxyethyl)-N-{1-[3-(1-naphthylmethyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-5-phenylpentanamide

Procedure

526 mg (2.37 mmol) of 2-(1-hydroxyethyl)-5-phenylpentanoic acid are reacted analogously to Example 39A with 320 mg (2.37 mmol) of 1-hydroxy-1H-benzotriazole, 408 mg (3.16 mmol) of N-ethyldiisopropylamine, 454 mg (6.350 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride and 500 mg (1.58 mmol) of 6-(1-aminoethyl)-3-(1-naphthylmethyl)-1,2,4-triazin-5(4H)-one to give 2-(1-hydroxyethyl)-N-{1-[3-(1-naphthylmethyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-5-phenylpentanamide.

Sources & evidence

ORD record
ord-f591f4b2b30c41c09fa3c44792c88d0b
Source dataset
uspto-grants-2003_06
Patent number
US06573263B2

Reaction notes

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