1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-Cyclopropyl-6,8-difluoro-5-methyl-7-[4-(1,2,3-triazol-1-yl)piperidin-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1742976

반응식

HRID 1742976 반응식
Cl.[N:2]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][N:4]=[N:3]1.C1CCN2C(=NCCC2)CC1.[CH:24]1([N:27]2[C:36]3[C:31](=[C:32]([CH3:40])[C:33]([F:39])=[C:34](F)[C:35]=3[F:37])[C:30](=[O:41])[C:29]([C:42]([OH:44])=[O:43])=[CH:28]2)[CH2:26][CH2:25]1>C(#N)C>[CH:24]1([N:27]2[C:36]3[C:31](=[C:32]([CH3:40])[C:33]([F:39])=[C:34]([N:10]4[CH2:11][CH2:12][CH:7]([N:2]5[CH:6]=[CH:5][N:4]=[N:3]5)[CH2:8][CH2:9]4)[C:35]=3[F:37])[C:30](=[O:41])[C:29]([C:42]([OH:44])=[O:43])=[CH:28]2)[CH2:25][CH2:26]1

참가 물질

5

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 146512581-Cyclopropyl-5-methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 190060184-(1H-1,2,3-triazol-1-yl)piperidine hydrochloride

생성물 1

HCID 190060391-Cyclopropyl-6,8-difluoro-5-methyl-7-[4-(1,2,3-triazol-1-yl)piperidin-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid수율 47.9%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

4-(1,2,3-triazol-1-yl)piperidine hydrochloride (126 mg, 0.66 mmol) and DBU (130 mg, 0.85 mmol) were added to a suspension of 1-cyclopropyl-5-methyl-6,7,8-trifluoro -1,4-dihydro-4-oxoquinoline-3-carboxylic acid (100 mg, 0.34 mmol) in acetonitrile (10 ml). The reaction mixture was refluxed for 24 hrs and then concentrated to dryness. The reaction was diluted with water. The separated solid was filtered and washed with water, acetonitrile and dried to give 70 mg of desired product. m.p. 261°-263° C.; 1H NMR (TFA) δ: 9.36 (s, 1H), 8.55 (s, 1H), 8.62 (s, 1H), 5.25 (m, 1H), 4.60 (m, 1H), 4.12 (m, 2H), 3.80 (m, 2H), 2.94 (s, 3H), 2.60 (m, 4H), 1.30-1.68 (m, 4H).

후처리

  1. temperatureThe reaction mixture was refluxed for 24 hrs
  2. concentrationconcentrated to dryness
  3. additionThe reaction was diluted with water
  4. filtrationThe separated solid was filtered
  5. washwashed with water, acetonitrile
  6. customdried

출처 및 근거

ORD 기록
ord-99736fe18dad430da45c76b6a032a228
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05342846

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