Dicyclohexylcarbodiimide → N-[4-(3-Bromopropoxy)phenyl]-9,10-dihydro-9-oxo-4-acridinecarboxamide

HRID 1451644노트

반응식

HRID 1451644 반응식
[O:1]=[C:2]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:16](O)=[O:17])[C:10]=2[NH:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.ON1C2C=CC=CC=2N=N1.[Br:29][CH2:30][CH2:31][CH2:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([NH2:40])=[CH:36][CH:35]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[Br:29][CH2:30][CH2:31][CH2:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([NH:40][C:16]([C:11]2[C:10]3[NH:9][C:8]4[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=4)[C:2](=[O:1])[C:15]=3[CH:14]=[CH:13][CH:12]=2)=[O:17])=[CH:36][CH:35]=1

참가 물질

6

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 35607584-Carboxy-9-acridanoneHCID 199745634-(3-Bromopropoxy)aniline

생성물 1

HCID 15299131N-[4-(3-Bromopropoxy)phenyl]-9,10-dihydro-9-oxo-4-acridinecarboxamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 9,10-dihydro-9-oxo-4-acridinecarboxylic acid (1.5 g) and 1-hydroxybenzotriazole (1.1 g) in DMF (50 ml) was stirred at room temperature for 10 min. The product of part (ii) above (1.5 g) was then added followed by dicyclohexylcarbodiimide (1.3 g), and the mixture was stirred at room temperature for 16 h and then filtered. The filtrate was concentrated in vacuo, treated with water and extracted with dichloromethane. The combined, dried organic extracts were concentrated to give the title compound (0.5 g) which was recrystallised from acetonitrile, MP 126°.

후처리

  1. stirringthe mixture was stirred at room temperature for 16 h
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. additiontreated with water
  5. extractionextracted with dichloromethane
  6. concentrationdried organic extracts were concentrated

출처 및 근거

ORD 기록
ord-87016f6b3580417eabca14c9e3f9c9a1
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05604237

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