1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-Cyclopropyl-6-fluoro-7-(3-(1, 2, 3-triazol-1-yl) pyrrolidin-1-yl]-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid

HRID 1742939

反応式

HRID 1742939 の反応式
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11](F)[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1.C1CCN2C(=NCCC2)CC1.Cl.[N:32]1([CH:37]2[CH2:41][CH2:40][NH:39][CH2:38]2)[CH:36]=[CH:35][N:34]=[N:33]1>N1C=CC=CC=1>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11]([N:39]4[CH2:40][CH2:41][CH:37]([N:32]5[CH:36]=[CH:35][N:34]=[N:33]5)[CH2:38]4)[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 52104221-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 190059431-(pyrrolidin-3-yl)-1H-1,2,3-triazole hydrochloride

生成物 1

HCID 543384181-Cyclopropyl-6-fluoro-7-(3-(1, 2, 3-triazol-1-yl) pyrrolidin-1-yl]-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
80 °C

実験手順

A mixture of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid (120 mg, 0.486 mmol), DBU (190 mg, 1.25 mmol), 3-(1,2,3-triazol-1-yl)pyrrolidine hydrochloride (216 mg, 1.25 mmol) in pyridine (8 ml) was heated at 80° C. for 18 h. The reaction mixture was concentrated and treated with water. The separated solid was collected by filtration, washed with water and acetonitrile to give light brown solid. Yield: 71 mg (38%), m.p. 284° C. (dec). 1H NMR (TFA) δ: 1.5 (m, 4H), 3.0 (m, 2H), 4.0 (m, 4H), 4.65 (bs, 1H), 5.9 (bs, 1H), 7.5 (d, 1H),8.20 (d, 1H), 8.6 (s, 1H), 8.7 (s, 1H), 9.2 (S, 1H).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. additiontreated with water
  3. filtrationThe separated solid was collected by filtration
  4. washwashed with water and acetonitrile
  5. customto give light brown solid

出典と根拠

ORDレコード
ord-68661dba03084cbb93a56396af9c98a9
出典データセット
uspto-grants-1994_08
特許番号
US05342846

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