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

HRID 1742969노트

반응식

HRID 1742969 반응식
[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:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.Cl.[C:23]1([C:29]2[N:30]=[N:31][N:32]([CH:34]3[CH2:38][CH2:37][NH:36][CH2:35]3)[CH:33]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[N+](=C1CCCCCCCCCC1C1CCCCCCCCCC1)=[N-]>N1C=CC=CC=1>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:36]2[CH2:37][CH2:38][CH:34]([N:32]3[CH:33]=[C:29]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:30]=[N:31]3)[CH2:35]2)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:16][CH2:17]1

참가 물질

5

반응물 3

HCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 190060374-phenyl-1-(pyrrolidin-3-yl)-1H-1,2,3-triazole hydrochlorideHCID 22171225Diazobicycloundecane

생성물 1

HCID 190059915-Amino-1-cyclopropyl-6,8-difluoro-7-[3-(4-Phenyl-1,2,3-triazol-1-yl)pyrrolidin-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid수율 10%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
90 °C

실험 절차

A mixture of 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid (100 mg, 0.33 mmol), 3-(4-phenyl-1,2,3-triazol-1-yl)pyrrolidine hydrochloride (160 mg, 0.42 mmol) and diazobicycloundecane (102 mg, 0.67 mmol) in pyridine (5 ml) was heated at 90° C. for 20 hrs. The reaction mixture was concentrated and the residue was diluted with water. The separated solid was filtered, washed with water, methanol and then with CHCl3, followed by acetonitrile to get 16 mg (10%) of title compound, m.p. 265° C. 1H NMR (TFA) δ: 0.92-1.43 (m, 4H), 2.51-2.80 (m, 2H), 3.57-4.59 (m, 5H), 5.43-5.62 (m, 1H), 7.44 (dd, 5H), 8.50 (s, 1H), 8.84 (s, 1H).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was diluted with water
  3. filtrationThe separated solid was filtered
  4. washwashed with water, methanol

출처 및 근거

ORD 기록
ord-9621506843b848f893c6409e79618fd2
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05342846

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