Triethylamine → (R)-7-[3-(1-Amino-1-methylethyl)-1-pyrrolidinyl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic Acid

HRID 1197995ノート

反応式

HRID 1197995 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18]2[C:13](=[C:14]([CH3:21])[C:15]([F:20])=[C:16](F)[CH:17]=2)[C:12](=[O:22])[C:11]([C:23]([OH:25])=[O:24])=[CH:10]1.C([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])C>C(#N)C>[NH2:9][C:3]([C@@H:32]1[CH2:30][CH2:29][N:28]([C:16]2[CH:17]=[C:18]3[C:13]([C:12](=[O:22])[C:11]([C:23]([OH:25])=[O:24])=[CH:10][N:9]3[C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[F:1])=[C:14]([CH3:21])[C:15]=2[F:20])[CH2:31]1)([CH3:4])[CH3:2]

参加物

4

反応物 2

HCID 8471TriethylamineHCID 14651285HCID 14651285、化合物

生成物 1

HCID 15230565(R)-7-[3-(1-Amino-1-methylethyl)-1-pyrrolidinyl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic Acid収率 244.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 0.92 g (2.62 mmol) of 1-(2,4-difluorophenyl)-6,7-difluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid, 0.90 g (3.9 mmol) of (3R)-(1,-methyl-1'-t-butoxycarbonylaminoethyl)pyrrolidine (9a), 0.80 g (7.9 mmol) of triethylamine, and 50 mL of acetonitrile was heated at reflux for 18 hours. The solution was cooled to room temperature and concentrated in vacuo to an orange solid. The residue was chromatographed on E. Merck silica gel (230-400 mesh), eluting with 90:10 CHCl3:MeOH to give 1.47 g of (R) 7-[3-(1-t-butoxycarbonylamino-1-methylethyl)-1-pyrrolidinyl]-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid; NMR (CDCl3) δ8.47 (s, 1 H), 7.44 (m, 1 H), 7.15 (m, 2 H), 5.64 (d, J=7 HZ, 1 H), 4.47 (bs, 1 H), 3.50- 3.20 (m, 4 H), 2.85 (d, J=3.5 HZ, 3 H), 1.91 (m, 1 H), 1.74 (m, 2 H), 1.42 (s, 9 H), 1.29 (d, J=11 HZ, 6 H).

後処理

  1. temperatureat reflux for 18 hours
  2. concentrationconcentrated in vacuo to an orange solid
  3. customThe residue was chromatographed on E
  4. washMerck silica gel (230-400 mesh), eluting with 90:10 CHCl3

出典と根拠

ORDレコード
ord-b79bb664d99f4e40a4f2e6f1d9846586
出典データセット
uspto-grants-1994_01
特許番号
US05278317

反応ノート

読み込み中…