1-Hydroxybenzotriazole → HCID 68841578, compound

HRID 1889278Notes

Reaction equation

HRID 1889278 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][C:12]=2[C:21](O)=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)C(C)C)(C)C.Cl.[CH3:56][O:57][C:58](=[O:63])[C:59]([NH2:62])([CH3:61])[CH3:60]>CN(C=O)C>[CH3:56][O:57][C:58](=[O:63])[C:59]([CH3:61])([NH:62][C:21]([C:12]1[CH:13]=[CH:14][C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:11]=1[NH:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:22])[CH3:60]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13258034Methyl 2-aminoisobutyrate hydrochlorideHCID 68846281HCID 68846281, compound

Product 1

HCID 68841578HCID 68841578, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under argon atmosphere 16 mg 1-(3-phenyl-propylamino)-naphthalene-2-carboxylic acid, 10 mg 1-hydroxybenzotriazole, 12 mg 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 18 μl of N,N-diisopropylethylamine in 1 ml of dry DMF were stirred at 0° C. After 30 minutes at 0° C. 8 mg of 2-aminoisobutyric acid methyl ester hydrochloride, followed by 18 μl of N,N-diisopropylethylamine were added. After 16 h at room temperature the reaction mixture was concentrated, and the residue was purified by RP-HPLC to yield 7 mg of 2-methyl-2-{[1-(3-phenyl-propylamino)-naphthalene-2-carbonyl]-amino}-propionic acid methyl ester.

Workup

  1. additionwere added
  2. concentrationAfter 16 h at room temperature the reaction mixture was concentrated
  3. customthe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-9fb256303be04e39ad1030066e42d82a
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

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