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

반응식

HRID 1742939 반응식
[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

참가 물질

5

반응물 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

생성물 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

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-68661dba03084cbb93a56396af9c98a9
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05342846

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