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

HRID 915587
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HRID 915587 반응식
[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]
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7

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매
HCID 962
Water
용매
HCID 8028Tetrahydrofuran용매

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온도
40 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5c7eafa6709c4256889b6c71f7f3076b
출처 데이터셋
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07265144B2

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