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

HRID 1742951

反応式

HRID 1742951 の反応式
[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.[CH3:23][C:24]1[N:25]=[N:26][N:27]([CH:29]2[CH2:33][CH2:32][NH:31][CH2:30]2)[CH:28]=1.C1CCN2C(=NCCC2)CC1>C(#N)C>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:31]2[CH2:32][CH2:33][CH:29]([N:27]3[CH:28]=[C:24]([CH3:23])[N:25]=[N:26]3)[CH2:30]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[CH2:17][CH2:16]1

参加物

5

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 190059493-(4-Methyl-1,2,3-triazol-1-yl)pyrrolidine hydrochloride

生成物 1

HCID 190059585-Amino-1-cyclopropyl-6,8-difluoro-7-[3-(4-methyl-1,2,3-triazol-1-yl)pyrrolidin-1-yl]-1,4,dihydro-4-oxoquinoline-3-carboxylic acid収率 46.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

5-Amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (298 mg, 1 mmol) was reacted with 470 mg (2.5 mmol) of 3-(4-methyl-1,2,3-triazol-1-yl)pyrrolidine hydrochloride in the presence of 380 mg (2.5 mmol) of DBU in 20 ml of dry acetonitrile for two days under reflux conditions and the atmosphere of nitrogen. The yellow suspension was then evaporated to dryness and to the residue water was added. The yellow solid was filtered and crystallized repeatedly (3x) with acetonitrile to free the product from the unreacted starting material. After drying, 200 mg of the desired product was obtained, m.p. 271°-272.5° C. 1H NMR (TFA) δ: 9.15 (s, 1H), 8.4 (s, 1H), 5.8-5.6 (m, 1H), 4.8-4.05 (m, 5H), 3.0-2.7 (m, 2H), 2.67 (s, 3H), 1.65-1.2 (m, 4H). Anal. calcd. for C20H20F2N6O3.1/2 H2O: C, 54.67; H, 4.82; N, 19.12. Found: C, 54.91; H, 4.69; N, 18.76.

後処理

  1. customThe yellow suspension was then evaporated to dryness and to the residue water
  2. additionwas added
  3. filtrationThe yellow solid was filtered
  4. customcrystallized repeatedly (3x) with acetonitrile
  5. customAfter drying

出典と根拠

ORDレコード
ord-48e5c61947824e68a15640f005732a71
出典データセット
uspto-grants-1994_08
特許番号
US05342846

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