Hydrochloric Acid → 6-[4-({3-[3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]propyl}oxy)phenyl]-2-quinolinecarboxylic acid

HRID 2423445ノート

反応式

HRID 2423445 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:25]=[C:26]4[C:31](=[CH:32][CH:33]=3)[N:30]=[C:29]([C:34]([O:36]C)=[O:35])[CH:28]=[CH:27]4)=[CH:20][CH:19]=2)=[C:12]([CH:38]([CH3:40])[CH3:39])[O:11][N:10]=1.O1CCCC1.[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[CH:25]=[C:26]4[C:31](=[CH:32][CH:33]=3)[N:30]=[C:29]([C:34]([OH:36])=[O:35])[CH:28]=[CH:27]4)=[CH:22][CH:23]=2)=[C:12]([CH:38]([CH3:40])[CH3:39])[O:11][N:10]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59321559Methyl 6-[4-({3-[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]propyl}oxy)phenyl]-2-quinolinecarboxylate

生成物 1

HCID 593214996-[4-({3-[3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]propyl}oxy)phenyl]-2-quinolinecarboxylic acid収率 89%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
90 °C

実験手順

To a solution of methyl 6-[4-({3-[3-(2,6-dichlorophenyl) -5-(1-methylethyl)-4-isoxazolyl]propyl}oxy)phenyl]-2-quinolinecarboxylate (14 mg, 0.024 mmol) in 1:1 tetrahydrofuran:methanol (1 mL) was added 1 N sodium hydroxide (0.089 mL, 0.089 mmol). The solution was heated in a microwave reactor at 90° C. for 10 minutes. Then 1 N hydrochloric acid (0.089 mL, 0.089 mmol) was added and the mixture was concentrated. Water and ethyl acetate were added to the residue and the layers were separated. The ethyl acetate layer was dried over magnesium sulfate and concentrated to afford 12 mg of 6-[4-({3-[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]propyl}oxy)phenyl]-2-quinolinecarboxylic acid as a yellow solid (0.021 mmol, 89%). 1H-NMR (400 MHz, DMSO-d6) δ 8.42 (d, J=9 Hz, 1H), 8.28 (d, J=9 Hz, 1H), 8.19 (d, J=9 Hz, 1H), 8.06-8.04 (m, 2H), 7.64 (d, J=9 Hz, 2H), 7.41-7.29 (m, 3H), 6.93 (d, J=9 Hz, 2H), 3.90 (t, J=6 Hz, 2H), 3.20 (septet, J=7 Hz, 1H), 2.52 (t, J=6 Hz, 2H), 1.83-1.77 (m, 2H), 1.34 (d, J=7 Hz, 6H). HRMS (ESI) C31H26Cl2N2O4 calculated: 561.1342 (M+H)+, found: 561.1344 (M+H)+.

後処理

  1. concentrationthe mixture was concentrated
  2. additionWater and ethyl acetate were added to the residue
  3. customthe layers were separated
  4. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-f1267a5a0aca4644919a7d4f7b5cc932
出典データセット
uspto-grants-2011_06
特許番号
US07960552B2

反応ノート

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