Cyclohexylamine → 6-Chloro-4-hydroxy-1-(4-methoxybenzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic Acid Cyclohexylamide

HRID 901271ノート

反応式

HRID 901271 の反応式
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O:10][C:11]([C:13]1[C:14](=[O:34])[N:15]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[C:16]2[C:21]([C:22]=1[OH:23])=[CH:20][C:19]([Cl:24])=[CH:18][N:17]=2)=O)C>C1(C)C(C)=CC=CC=1>[CH:1]1([NH:7][C:11]([C:13]2[C:14](=[O:34])[N:15]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[C:16]3[C:21]([C:22]=2[OH:23])=[CH:20][C:19]([Cl:24])=[CH:18][N:17]=3)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

4

反応物 2

HCID 7965CyclohexylamineHCID 547385986-Chloro-4-hydroxy-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic Acid Ethyl Ester

生成物 1

HCID 692188546-Chloro-4-hydroxy-1-(4-methoxybenzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic Acid Cyclohexylamide収率 89.3%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

反応条件

温度
140 °C

実験手順

Cyclohexylamine (6.15 mL, 53.70 mmol) was added to a stirred solution of 6-chloro-4-hydroxy-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (75) (10.44 g, 26.85 mmol) in xylene and heated at 140° C. for 3 h. The solution was cooled and the solvent was evaporated under vacuum. The residue was suspended in water and extracted by dichloromethane. The combined organic phase was washed by water and brine, then dried over Na2SO4 and evaporated to yield 10.6 g (89%) of 6-chloro-4-hydroxy-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid cyclohexylamide (93) as white solids. MP: 193° C.; 1H-NMR (CDCl3): δ 1.24-1.99 (m, 10H), 3.47 (s, 3H), 3.93 (m, 1H), 5.59 (s, 2H), 6.78 (m, 2H), 7.37 (m, 2H), 8.39 (d, J=2.4 Hz, 1H), 8.60 (d, J=2.4 Hz, 1H), 10.15 (s, 1H); EIMS m/z 442 (M+1).

後処理

  1. temperatureThe solution was cooled
  2. customthe solvent was evaporated under vacuum
  3. extractionextracted by dichloromethane
  4. washThe combined organic phase was washed by water and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated

出典と根拠

ORDレコード
ord-47ab53085b6c43e7a8b7dba0ff402ec2
出典データセット
uspto-grants-2008_04
特許番号
US07361760B2

反応ノート

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