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

HRID 1742949

反応式

HRID 1742949 の反応式
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:17])[C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.Cl.[N:23]1([CH:28]2[CH2:32][CH2:31][NH:30][CH2:29]2)[CH:27]=[N:26][CH:25]=[N:24]1.C1CCN2C(=NCCC2)CC1>N1C=CC=CC=1>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:17])[C:10]([F:16])=[C:11]([N:30]4[CH2:31][CH2:32][CH:28]([N:23]5[CH:27]=[N:26][CH:25]=[N:24]5)[CH2:29]4)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:2][CH2:3]1

参加物

5

反応物 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 190059941-(pyrrolidin-3-yl)-1H-1,2,4-triazole hydrochloride

生成物 1

HCID 190060051-Cyclopropyl-6,8-difluoro-5-methyl-7-[3-(1,2,4-triazol-1-yl)-pyrrolidin-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid収率 28.9%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

1-Cyclopropyl-5-methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (30 mg, 0.1 mmol) was reacted with 40 mg (0.2 mmol) of 3-(1,2,4-triazol-1-yl)pyrrolidine hydrochloride in 2 ml of pyridine in the presence of 70 mg (0.45 mmol) of DBU at 95° C. overnight. The orange solution was evaporated to dryness and to the residue water was added. The orange solid was collected and washed with methanol to yield 19 mg of the crude product, which upon further purification from methanol yielded 12 mg of the desired product. m.p. 207°-210° C. 1H NMR (TFA) δ: 9.81 (s, 1H), 9.27 (s, 1H), 8.78 (s, 1H), 5.75-5.55 (m, 1H), 4.83-4.12 (m, 5H), 3.0-2.7 (m, 5H), 1.7-1.2 (m, 4H). Anal. calcd. for C20H19F2N5O3H2O: C, 55.43; H, 4.88; N, 16.16. Found: C, 55.72; H, 4.73; N, 15.65.

後処理

  1. customThe orange solution was evaporated to dryness and to the residue water
  2. additionwas added
  3. customThe orange solid was collected
  4. washwashed with methanol
  5. customto yield 19 mg of the crude product, which
  6. customupon further purification from methanol

出典と根拠

ORDレコード
ord-e1be6c11a61e4b1dbaa32ef633c285cc
出典データセット
uspto-grants-1994_08
特許番号
US05342846

関連ノート

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