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Hydrochloric Acid → 2-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}-5-ethylbenzoic acid

HRID 915587
ノート
印刷プレビュー

反応式

HRID 915587 の反応式
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]2[CH:20]=[CH:19][C:18]([CH2:21][CH3:22])=[CH:17][C:12]=2[C:13]([O:15]C)=[O:14])[N:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].Cl>CO.C1COCC1.O>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]2[CH:20]=[CH:19][C:18]([CH2:21][CH3:22])=[CH:17][C:12]=2[C:13]([OH:15])=[O:14])[N:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[N:6]=1)([CH3:4])([CH3:2])[CH3:3]
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

7

反応物 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 58958598methyl 2-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}-5-ethylbenzoate

生成物 1

HCID 589585832-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}-5-ethylbenzoic acid収率 100.1%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒
HCID 962
Water
溶媒
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

To a solution of methyl 2-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}-5-ethylbenzoate (Example 235, 115 mg, 0.29 mmol) in a mixture of methanol (1 mL) and THF (1 mL) was added lithium hydroxide monohydrate (123 mg, 2.94 mmol) in water (2 mL), and the mixture was heated to 40° C. for 1 h. The reaction mixture was then cooled to rt, and the pH of the solution was adjusted to 5 using 0.5 N aq HCl. The solvent was removed under reduced pressure, and the residue was subjected to HPLC purification using gradient elution from 10% to 90% acetonitrile in water to afford 109.6 mg (99%) of the title compound. 1H NMR (300 MHz, CD2Cl2) δ 9.28 (s, 1H), 7.76 (s, 1H), 7.26-7.37 (m, 6H), 6.15 (s, 1H), 2.60 (q, 2H), 2.08 (s, 3H), 1.37 (s, 9H), 1.23 (t, 3H). ES-MS m/z 378.3 (MH+); HPLC RT (min) 3.64.

後処理

  1. temperatureThe reaction mixture was then cooled to rt
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was subjected to HPLC purification
  4. washelution from 10% to 90% acetonitrile in water

出典と根拠

ORDレコード
ord-5c7eafa6709c4256889b6c71f7f3076b
出典データセット
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07265144B2

反応ノート

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