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Hydrochloric Acid → 5-methoxy-1-(5-(((tetrahydro-2 H-pyran-4-yl)methyl)carbamoyl)pyridin-2-yl)-1H-pyrazole-4-carboxylic acid

HRID 526428
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HRID 526428 반응식
[CH3:1][O:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:23])[NH:15][CH2:16][CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:10][N:9]=2)[N:6]=[CH:5][C:4]=1[C:24]([O:26]CC)=[O:25].[Li+].[OH-].Cl>O1CCOCC1>[CH3:1][O:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:23])[NH:15][CH2:16][CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:10][N:9]=2)[N:6]=[CH:5][C:4]=1[C:24]([OH:26])=[O:25]
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참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 117600311ethyl 5-methoxy-1-(5-(((tetrahydro-2H-pyran-4-yl)methyl)carbamoyl)pyridin-2-yl)-1H-pyrazole-4-carboxylate

생성물 1

HCID 1176002455-methoxy-1-(5-(((tetrahydro-2 H-pyran-4-yl)methyl)carbamoyl)pyridin-2-yl)-1H-pyrazole-4-carboxylic acid수율 91.4%

시약·촉매·용매 1

HCID 31275
1,4-Dioxane
용매

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온도
23 °C

실험 절차

Combined ethyl 5-methoxy-1-(5-(((tetrahydro-2H-pyran-4-yl)methyl)carbamoyl)pyridin-2-yl)-1H-pyrazole-4-carboxylate (401 mg, 1.032 mmol), dioxane (7 mL) and 1M aqueous LiOH (5.16 mL, 5.16 mmol) at 23° C. The reaction mixture was stirred at 23° C. for 3 hours, and then quenched with 1N HCl (aq.) (5.16 mL, 5.16 mmol), and concentrated via rotary evaporation to furnish an off-white suspension. The suspension was filtered, rinsed with water (5×3 mL), and dried in vacuo to give the title compound (339.8 mg, 91% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.16-1.28 (m, 2H) 1.58-1.67 (m, 2H) 1.75-1.88 (m, 1H) 3.20 (t, J=6.32 Hz, 2H) 3.27 (td, J=11.62, 2.02 Hz, 2H) 3.82-3.90 (m, 2H) 4.14 (s, 3H) 7.78 (dd, J=8.59, 0.76 Hz, 1H) 7.98 (s, 1H) 8.40 (dd, J=8.46, 2.40 Hz, 1H) 8.78 (t, J=5.81 Hz, 1H) 8.98 (dd, J=2.40, 0.63 Hz, 1H) 12.68 (s, 1H). MS m/z [M+H]+ 361.4.

후처리

  1. customat 23° C
  2. concentrationconcentrated via rotary evaporation
  3. customto furnish an off-white suspension
  4. filtrationThe suspension was filtered
  5. washrinsed with water (5×3 mL)
  6. customdried in vacuo

출처 및 근거

ORD 기록
ord-9c295a6011684a4c87654db7a0ec3951
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09345713B2

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