Triethylamine → HCID 15670689、化合物

HRID 729062ノート

反応式

HRID 729062 の反応式
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.[C:21]([NH:24][CH:25]1[CH2:30][CH2:29][CH2:28][NH:27][CH2:26]1)(=[O:23])[CH3:22].C(N(CC)CC)C>CS(C)=O>[C:21]([NH:24][CH:25]1[CH2:30][CH2:29][CH2:28][N:27]([C:11]2[C:12]([F:14])=[C:13]3[C:8]([C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5][N:4]3[CH:1]3[CH2:2][CH2:3]3)=[CH:9][C:10]=2[F:16])[CH2:26]1)(=[O:23])[CH3:22]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 41697193-Acetamidopiperidine

生成物 1

HCID 15670689HCID 15670689、化合物収率 66.6%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
100 °C

実験手順

A mixture of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid(566 mg), 3-acetamidopiperidine (300 mg), triethylamine (220 mg) and dimethylsulfoxide (10 ml) was heated at 100° C. for 2 hours with stirring. Thereafter the mixture was cooled to room temperature and ice water was added thereto. The precipitated crystalline was filtered off andwashed with methanol-ether to give 7-(3-acetamidopiperidin-1-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (540 mg) (m.p. 280°-282° C., recrystallized from methanol). The product (405 mg) obtained in the above manner was suspended in 6N hydrochloric acid (5 ml) and heated at 100° C. for 2.5 hours with stirring. The reaction mixture was further processed in a similar manner to step (b) of Example 1 to afford hydrochloride of 7-(3-aminopiperidinly-1)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. The physical properties of this product were identical with those of the compound provided in Example 1.

後処理

  1. temperatureThereafter the mixture was cooled to room temperature
  2. filtrationThe precipitated crystalline was filtered off andwashed with methanol-ether

出典と根拠

ORDレコード
ord-6cc11e4c3bbc4a9ea134231e059a1c88
出典データセット
uspto-grants-1991_09
特許番号
US05051509

反応ノート

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