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Triethylamine → 5-Amino-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(4-methylamino-3,3-dimethyl-1-piperidinyl)-4-oxo-quinoline-3-carboxylic Acid

HRID 746915
ノート
印刷プレビュー

反応式

HRID 746915 の反応式
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:22])[C:5]([C:19]([OH:21])=[O:20])=[CH:6][N:7]2[CH:16]1[CH2:18][CH2:17]1.[CH3:23][C:24]1([CH3:32])[CH:29]([NH:30][CH3:31])[CH2:28][CH2:27][NH:26][CH2:25]1.C(N(CC)CC)C>CS(C)=O.C(#N)C>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:26]2[CH2:27][CH2:28][CH:29]([NH:30][CH3:31])[C:24]([CH3:32])([CH3:23])[CH2:25]2)[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:22])[C:5]([C:19]([OH:21])=[O:20])=[CH:6][N:7]2[CH:16]1[CH2:18][CH2:17]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 10125063HCID 10125063、化合物HCID 105668945-Amino-1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

生成物 1

HCID 101376665-Amino-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(4-methylamino-3,3-dimethyl-1-piperidinyl)-4-oxo-quinoline-3-carboxylic Acid

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide
溶媒
HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

A suspension of 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-quinoline-3-carboxylic acid (0.17 g, 0.55 mmol), 3,3-dimethyl-4-methylamino piperidine (0.15 g, 1.06 mmol) and triethylamine (1 g, 10 mmol) in a mixture of dimethylsulfoxide (10 ml) and acetonitrile (10 ml) was heated at 70° C. for 18 hr. Acetonitrile was distilled off, filtered to remove suspended impurities, diluted with water (5 ml). The precipitate thus separated was filtered, washed with water, dried and purified by silicagel column chromatography. Elute from a mixture of ethyl acetate and methanol furnished the required product. Yield 0.12 g (50%), m.p. 250° C. (decomp.), C22H29FN4O4, m/z 433 (M+1), PMR (DMSO-d6): 0.9 (m, 2H), 1.0 (m, 2H), 1.0 (s, 3H), 1.1 (s, 3H), 1.8-2.0 (m, 2H), 2.6 (s, 3H), 2.8-3.2 (m, 4H), 3.5 (s, 3H), 3.6 (s, 3H), 3.65 (m, 1H), 4.0 (m, 1H), 7.2 (bs, 2H, D2O exchangeable), 8.6 (s, 1H).

後処理

  1. distillationAcetonitrile was distilled off
  2. filtrationfiltered
  3. customto remove
  4. additiondiluted with water (5 ml)
  5. customThe precipitate thus separated
  6. filtrationwas filtered
  7. washwashed with water
  8. customdried
  9. custompurified by silicagel column chromatography
  10. washElute from a mixture of ethyl acetate and methanol

出典と根拠

ORDレコード
ord-db339a5275994fffa49576209fe49686
出典データセット
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07393957B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート