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1-Hydroxybenzotriazole → 2-(6-quinolinyloxy)-2-(ethoxy)-N-(2-methylpent-3-yn-2-yl) acetamide

HRID 1244808
Notes
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Reaction equation

HRID 1244808 reaction equation
Cl.[NH2:2][C:3]([CH3:8])([CH3:7])[C:4]#[C:5][CH3:6].[N:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH:20]([O:24][CH2:25][CH3:26])[C:21](O)=[O:22])=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O.O.C(N(CC)CC)C>[N:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH:20]([O:24][CH2:25][CH3:26])[C:21]([NH:2][C:3]([CH3:8])([C:4]#[C:5][CH3:6])[CH3:7])=[O:22])=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 219231292-Methylpent-3-yn-2-amine hydrochlorideHCID 219231312-(6-Quinolinyloxy)-2-(ethoxy)acetic acid

Product 1

HCID 692530452-(6-quinolinyloxy)-2-(ethoxy)-N-(2-methylpent-3-yn-2-yl) acetamideYield 88.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Triethylamine (0.3 ml) was added to a stirred solution of 4-amino-4-methylpent-2-yne hydrochloride (0.054 g) in N,N-dimethylformamide (2 ml) giving a white suspension. 2-(6-Quinolinoxy)-2-(ethoxy)acetic acid (0.1 g) was added followed by N-(3-dimethylaminopropyl)-N′-ethyl carbodiimide hydrochloride (0.077 g) and a catalytic amount of 1-hydroxybenzotriazole (0.005 g), and the white suspension was stirred at ambient temperature for 18 hours. Water was added and the aqueous phase was extracted with ethyl acetate. The organic phase was washed with water, saturated aqueous sodium bicarbonate and brine, dried over magnesium sulphate and evaporated under reduced pressure to give a yellow oil (0.117 g). The oil was purified by flash chromatography (silica gel; ethyl acetate/hexane, 1:1 by volume) to give the required product (0.096 g) as a colourless oil.

Workup

  1. customgiving a white suspension
  2. extractionthe aqueous phase was extracted with ethyl acetate
  3. washThe organic phase was washed with water, saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9423977cd3bd46c1b6720cb30ab8a361
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07122672B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes