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Methanesulfonyl chloride → 3-{4-[4-(2-oxo-2H-1-benzopyran-6-yl)-1-piperazinyl]butyl}-5-fluoroindole, hydrochloride

HRID 1068688
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HRID 1068688 반응식
CS(O[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:19])[CH:17]=2)[NH:12][CH:11]=1)(=O)=O.FC1C=C2C(=CC=1)NC=C2CCCCO.[H-].[Al+3].[Li+].[H-].[H-].[H-].FC1C=C2C(=CC=1)NC=C2CCCC(O)=O.CS([Cl:61])(=O)=O.Cl.[O:63]=[C:64]1[CH:69]=[CH:68][C:67]2[CH:70]=[C:71]([N:74]3[CH2:79][CH2:78][NH:77][CH2:76][CH2:75]3)[CH:72]=[CH:73][C:66]=2[O:65]1>C1COCC1.C(N(CC)CC)C.C(#N)C>[ClH:61].[O:63]=[C:64]1[CH:69]=[CH:68][C:67]2[CH:70]=[C:71]([N:74]3[CH2:75][CH2:76][N:77]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]4[C:18]5[C:13](=[CH:14][CH:15]=[C:16]([F:19])[CH:17]=5)[NH:12][CH:11]=4)[CH2:78][CH2:79]3)[CH:72]=[CH:73][C:66]=2[O:65]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 6

HCID 31297Methanesulfonyl chlorideHCID 111088894-(5-Fluoroindol-3-yl)butyl methanesulfonateHCID 150472684-(5-Fluoro-1H-indol-3-yl)butanoic acidHCID 183302714-(5-fluoro-1H-indol-3-yl)butan-1-olHCID 21226445Aluminium lithium hydrideHCID 1317227094-(2-oxo-2H-1-benzopyran-6-yl)piperazine, hydrochloride

생성물

1
HCID 111785583-{4-[4-(2-oxo-2H-1-benzopyran-6-yl)-1-piperazinyl]butyl}-5-fluoroindole, hydrochloride

시약·촉매·용매 3

HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

실험 절차

A mixture of 5.10 g (0.017 mol) of 4-(5-fluoroindol-3-yl)butyl methanesulfonate [obtainable by reaction of 4-(5-fluoroindol-3-yl)butanol (obtainable by lithium aluminium hydride reduction of 4-(5-fluoroindol-3-yl)butanoic acid, which can be prepared analogously to a Japp-Klingemann reaction, in THF) with methanesulfonyl chloride], 4.0 g (0.015 mol) of 4-(2-oxo-2H-1-benzopyran-6-yl)piperazine, hydrochloride (obtainable as described in Example 1), 200 ml of acetonitrile and 10.0 ml of triethylamine is reacted for 30 hours on a steam bath with stirring. After customary working up, 3-{4-[4-(2-oxo-2H-1-benzopyran-6-yl)-1-piperazinyl]butyl}-5-fluoroindole, hydrochloride, m.p. 293-295°, is obtained.

후처리

  1. customis reacted for 30 hours on a steam bath

출처 및 근거

ORD 기록
ord-a1ba928dcce741318c149cd8af38cedd
출처 데이터셋
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06251908B1

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