반응 #338865

ord-43255ec01a934ae8ae91ad6bec7f4ef2

반응 방정식

O=C1Nc2ccc(F)cc2C1=NN=Cc1ccc(C(=O)O)cc1
4-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)benzoic acid
CCN=C=NCCCN(C)C.Cl
1-Ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride
Oc1cccc2[nH]nnc12
hydroxybenzo-triazole
CCN(CC)CC
triethylamine
COC(=O)CCCCCN.Cl
6-aminocaproic acid methyl ester hydrochloride
COC(=O)CCCCCNC(=O)c1ccc(C=NN=C2C(=O)Nc3ccc(F)cc32)cc1
title compound
수율 28.0%
COC(=O)CCCCCNC(=O)c1ccc(C=NN=C2C(=O)Nc3ccc(F)cc32)cc1
6-(4-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)benzamido)-hexanoic acid methyl ester
수율 28.0%

용매

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    workup.ADDITIONwere added
  2. 2
    여과The solids were collected by vacuum filtration
  3. 3
    세척washed with water
  4. 4
    기타dried under vacuum

실험 절차

4-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)benzoic acid (311 mg, 1 mmol) and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (394 mg, 2 mmol), hydroxybenzo-triazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and 6-aminocaproic acid methyl ester hydrochloride (219 mg, 1.2 mmol) were added. The mixture was stirred for 24 hours at room temperature. The mixture was diluted with 400 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (114 mg, 28% yield) as a brown solid. LC-MS (m/z) 439 (M+1).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07863315B2uspto-grants-2011_01