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Hydrochloric Acid → 6-[4-({[5-Cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid

HRID 2423411
ノート
印刷プレビュー

反応式

HRID 2423411 の反応式
[CH:1]1([C:6]2[O:10][N:9]=[C:8]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[C:7]=2[CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:28]=[C:29]4[C:34](=[CH:35][CH:36]=3)[N:33]=[C:32]([C:37]([O:39]C)=[O:38])[CH:31]=[CH:30]4)=[CH:23][CH:22]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.O1CCCC1.[OH-].[Na+].Cl>C(OCC)(=O)C.O.CO>[CH:1]1([C:6]2[O:10][N:9]=[C:8]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[C:7]=2[CH2:19][O:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]3[CH:28]=[C:29]4[C:34](=[CH:35][CH:36]=3)[N:33]=[C:32]([C:37]([OH:39])=[O:38])[CH:31]=[CH:30]4)=[CH:25][CH:26]=2)[CH2:2][CH2:3][CH2:4][CH2:5]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

8

反応物 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59321578Methyl 6-[4-({[5-cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate

生成物 1

HCID 593214686-[4-({[5-Cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid収率 82%

試薬・触媒・溶媒

3
HCID 887Methanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

To a solution of methyl 6-[4-({[5-cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (73 mg, 0.13 mmol) in 2:1 tetrahydrofuran:methanol (1.5 mL) was added 1N sodium hydroxide (0.19 mL, 0.19 mmol). A solid was seen to precipitate. The mixture was heated in a microwave reactor at 120° C. for 500 seconds and then was concentrated and the residue was taken up with water and hydrochloric acid (0.19 mL, 0.19 mmol) was added. Ethyl acetate was added and the layers were separated. The aqueous layer was extracted once more with ethyl acetate. The combined organic layers were washed with brine and concentrated to afford 6-[4-({[5-cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid (58 mg, 82%). 1H-NMR (400 MHz, DMSO-d6) δ 13.36 (br s, 1H), 8.53 (d, J=9 Hz, 1H), 8.27 (s, 1H), 8.18-8.08 (m, 3H), 7.73 (d, J=9 Hz, 2H), 7.63-7.51 (m, 3H), 6.92 (d, J=9 Hz, 2H), 4.87 (s, 2H), 3.59-3.51 (m, 1H), 2.11-2.03 (m, 2H), 1.84-1.64 (m, 6H). HRMS (ESI) C31H24Cl2N2O4 calculated: 559.1186 (M+H)+, found: 559.1183 (M+H)+.

後処理

  1. customto precipitate
  2. concentrationwas concentrated
  3. additionwas added
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted once more with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-fd25e6a64bff43eea05ee3f89fa5cf9e
出典データセット
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07960552B2

反応ノート

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