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

HRID 1742940

반응식

HRID 1742940 반응식
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.C1CCN2C(=NCCC2)CC1.Cl.[N:33]1([CH:38]2[CH2:42][CH2:41][NH:40][CH2:39]2)[CH:37]=[CH:36][N:35]=[N:34]1>N1C=CC=CC=1>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:40]4[CH2:41][CH2:42][CH:38]([N:33]5[CH:37]=[CH:36][N:35]=[N:34]5)[CH2:39]4)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:2][CH2:3]1

참가 물질

5

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 190059431-(pyrrolidin-3-yl)-1H-1,2,3-triazole hydrochloride

생성물 1

HCID 190059341-Cyclopropyl-6,8-difluoro-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
7580 °C

실험 절차

A mixture of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid (138.5 mg, 0.486 mmol), DBU (190 mg, 1.25 mmol), and 3-(1,2,3-triazol-1-yl)pyrrolidine hydrochloride (216 mg, 1.25 mmol) in pyridine (8 ml) was heated for 20 h at 7580° C. and then pyridine was removed under vacuum. The residue was diluted with acetonitrile. The precipitated solid was washed with acetonitrile, ether and dried at 40° C. Yield: 65 mg (33%), m.p. 244°-246° C. (dec). 1H NMR (TFA) δ: 1.5 (m, 4H), 2.8 (m, 2H), 4.5 (m, 4H), 4.75 (bs, 1H), 5.8 (bs, 1H), 8.15 (d, 1H), 8.6 (s, 1H), 8.7 (s, 1H), 9.25 (s, 1H).

후처리

  1. custompyridine was removed under vacuum
  2. additionThe residue was diluted with acetonitrile
  3. washThe precipitated solid was washed with acetonitrile, ether
  4. customdried at 40° C

출처 및 근거

ORD 기록
ord-6b1ff790fcf94f9f8ec5e26b002ef706
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05342846

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