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

HRID 1742942노트

반응식

HRID 1742942 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.[NH2:21][C@H:22]1[C@@H:26]([N:27]2[CH:31]=[CH:30][N:29]=[N:28]2)[CH2:25][NH:24][CH2:23]1>N1C=CC=CC=1>[NH2:21][C@H:22]1[C@@H:26]([N:27]2[CH:31]=[CH:30][N:29]=[N:28]2)[CH2:25][N:24]([C:11]2[C:12]([F:14])=[C:13]3[C:8]([C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5][N:4]3[CH:1]3[CH2:3][CH2:2]3)=[CH:9][C:10]=2[F:16])[CH2:23]1

참가 물질

4

반응물 2

HCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 70283180rac-(3R,4S)-4-(1H-1,2,3-triazol-1-yl)pyrrolidin-3-amine

생성물 1

HCID 702851867-[cis-3-Amino-4-(1,2,3-triazol-1-yl)-pyrrolidin-1-yl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
110 °C

실험 절차

A mixture of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid (44 mg, 0.156 mmol) and cis-3-amino-4-(1,2,3-triazol-1-yl)pyrrolidine (60 mg, 0.39 mmol) in pyridine (5 ml) was heated at 110° C. for 2-3 h under nitrogen and then stirred at room temperature for 20 h. The reaction mixture was concentrated and the residue was washed with water and acetonitrile. The solid was dried under vacuum at 40° C. Yield: 43 mg (66%), m.p. 245°-47° C. 1H NMR (TFA) δ: 1.3-1.8 (m, 4H), 4.4-5.25 (m, 6H), 6.40 (m, 1H), 8.15 (d, 1H), 8.62 (s, 1H), 8.90 (s, 1H), 9.40 (s, 1H).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. washthe residue was washed with water and acetonitrile
  3. customThe solid was dried under vacuum at 40° C

출처 및 근거

ORD 기록
ord-06b794bd6f2346aea2d48210744ab134
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05342846

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