5-Amino-1-(2,4-difluorophenyl)-6,7,8-trifluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid → 5-Amino-1-(2,4-difluorophenyl)-6,8-difluoro-7-[3-(1,2,3-triazol-1-yl]pyrrolidin-1-yl]-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid

HRID 1742941

反応式

[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:26])[C:5]([C:23]([OH:25])=[O:24])=[CH:6][N:7]2[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[F:22].Cl.[N:28]1([CH:33]2[CH2:37][CH2:36][NH:35][CH2:34]2)[CH:32]=[CH:31][N:30]=[N:29]1.N1(C2CCCCCCCCCC2)CCCCCCCCCN1>C(#N)C>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:35]2[CH2:36][CH2:37][CH:33]([N:28]3[CH:32]=[CH:31][N:30]=[N:29]3)[CH2:34]2)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:26])[C:5]([C:23]([OH:25])=[O:24])=[CH:6][N:7]2[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[F:22]

参加物

実験手順

A mixture of 5-amino-1-(2,4-difluorophenyl) -6,7,8-trifluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid (200 mg, 0.54 mmol), 3-(1,2,3-triazol-1-yl)pyrrolidine hydrochloride (231 mg, 1.25 mmol) and diazabicycloundecane (200 mg, 1.31 mmol) in acetonitrile (25 ml) was refluxed for 45 h. The separated solid was filtered, washed with acetonitrile and ether to give 150 mg (57%) of desired product, m.p. 307.5°-309° C. 1H NMR (TFA) δ: 2.81 (m, 2H), 4.06-4.53 (m, 4H), 5.73 (m, 1H), 7.15-7.23 (m, 2H), 7.59-7.66 (m, 1H), 8.52 (d, 1H), 8.62 (d, 1H), 8.82 (d, 1H).

後処理

temperaturewas refluxed for 45 h
filtrationThe separated solid was filtered
washwashed with acetonitrile and ether

出典と根拠

ORDレコード: ord-01aa3e14f04b4026b239b7443c1624c3
出典データセット: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US05342846

反応式

参加物

反応物 3

生成物 1

試薬・触媒・溶媒 1

実験手順

後処理

出典と根拠

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