Solketal → (2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 1-cyclopropyl-6-fluoro-4-oxo-7-(4-propylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylate

HRID 41818

反応式

HRID 41818 の反応式
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:23])=[C:11]([N:14]4[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH3:22])[CH2:16][CH2:15]4)[CH:12]=3)[C:7](=[O:24])[C:6]([C:25]([OH:27])=[O:26])=[CH:5]2)[CH2:3][CH2:2]1.[CH3:28][C:29]1([CH3:36])[O:33][CH:32]([CH2:34]O)[CH2:31][O:30]1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>ClCCl>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:23])=[C:11]([N:14]4[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH3:22])[CH2:16][CH2:15]4)[CH:12]=3)[C:7](=[O:24])[C:6]([C:25]([O:27][CH2:34][CH:32]3[CH2:31][O:30][C:29]([CH3:36])([CH3:28])[O:33]3)=[O:26])=[CH:5]2)[CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 7528SolketalHCID 8471TriethylamineHCID 4716651-Cyclopropyl-6-fluoro-4-oxo-7-(4-propylpiperazin-1-yl)quinoline-3-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 58455287(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 1-cyclopropyl-6-fluoro-4-oxo-7-(4-propylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylate収率 89%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

1-cyclopropyl-6-fluoro-4-oxo-7-(4-propylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid (8.86 g, 23.70 mmol) was dissolved in anhydrous dichloromethane (370 ml) under argon. 2,2-dimethyl-1,3-dioxolane-4-methanol (4.71 g, 35.60 mmol), triethylamine (9.59 g, 94.80 mmol) and HBTU (9.90 g, 26.10 mmol) were added and the reaction mixture was stirred at room temperature for three days (exclusion of light). The reaction mixture was washed with saturated NaHCO3 solution (500 ml), aqueous (pH 5) hydrochloric acid (500 ml) and water (500 ml) successively. The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure, yielding 10.28 g (89%) of a yellow solid.

後処理

  1. washThe reaction mixture was washed with saturated NaHCO3 solution (500 ml), aqueous (pH 5) hydrochloric acid (500 ml) and water (500 ml) successively
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-e80040af873245e5a8f1caffa4a02975
出典データセット
uspto-grants-2013_09
特許番号
US08535655B2

関連ノート

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