Hydrochloric Acid → HCID 59321498、化合物

HRID 2423465ノート

反応式

HRID 2423465 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]([CH2:16][C:17]1[C:21]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:31]=[C:32]4[C:37](=[CH:38][CH:39]=3)[N:36]=[C:35]([C:40]([O:42]C)=[O:41])[CH:34]=[CH:33]4)=[CH:26][CH:25]=2)=[C:20]([CH:44]([CH3:46])[CH3:45])[O:19][N:18]=1)C(=O)C(F)(F)F.O1CCCC1.[OH-].[Na+].Cl>O.CO>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[NH:9][CH2:16][C:17]1[C:21]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:31]=[C:32]4[C:37](=[CH:38][CH:39]=3)[N:36]=[C:35]([C:40]([OH:42])=[O:41])[CH:34]=[CH:33]4)=[CH:26][CH:25]=2)=[C:20]([CH:44]([CH3:46])[CH3:45])[O:19][N:18]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59321544Methyl 6-[4-({[3-{[(2,6-dichlorophenyl)(trifluoroacetyl)amino]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate

生成物 1

HCID 59321498HCID 59321498、化合物収率 100%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

To a solution of methyl 6-[4-({[3-{[(2,6-dichlorophenyl)(trifluoroacetyl)amino]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (10 mg, 0.015 mmol) in 1:1 tetrahydrofuran:methanol (0.75 mL) was added 1 N sodium hydroxide (0.37 mL, 0.37 mmol). The solution was heated in a microwave reactor at 90° C. for 10 minutes. The solution was concentrated and the residue was taken up with ethyl acetate. Then 1 N hydrochloric acid (0.37 mL, 0.37 mmol) was added followed by water. The layers were separated and the aqueous layer was extracted one more time with ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated to afford 6-[4-({[3-{[(2,6-dichlorophenyl)amino]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid (8 mg, 100%). 1H-NMR (400 MHz, CDCl3) δ 8.46 (d, J=9 Hz, 1H), 8.31-8.24 (m, 2H), 8.11-8.07 (m, 2H), 7.69 (d, J=9 Hz, 2H), 7.25-7.20 (m, 2H), 7.07 (d, J=9 Hz, 2H), 6.84-6.80 (m, 1H), 4.96 (s, 2H), 4.60 (s, 2H), 3.24 (septet, J=7 Hz, 1H), 1.36 (d, J=7 Hz, 6H). HRMS (ESI) C30H25Cl2N3O4 calculated: 562.1300 (M+H)+, found: 562.1292 (M+H)+.

後処理

  1. concentrationThe solution was concentrated
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted one more time with ethyl acetate
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-422f5dfe447949ce8b7348c7b1e1e8bc
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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