Hydrochloric Acid → N-(1-(2-oxoethyl)-1H-pyrazol-4-yl)-5-(m-tolyl)oxazole-4-carboxamide

HRID 624085

반응식

HRID 624085 반응식
C[O:2][CH:3](OC)[CH2:4][N:5]1[CH:9]=[C:8]([NH:10][C:11]([C:13]2[N:14]=[CH:15][O:16][C:17]=2[C:18]2[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=2)=[O:12])[CH:7]=[N:6]1.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[O:2]=[CH:3][CH2:4][N:5]1[CH:9]=[C:8]([NH:10][C:11]([C:13]2[N:14]=[CH:15][O:16][C:17]=2[C:18]2[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=2)=[O:12])[CH:7]=[N:6]1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86704230N-(1-(2,2-dimethoxyethyl)-1H-pyrazol-4-yl)-5-(m-tolyl)oxazole-4-carboxamide

생성물 1

HCID 86704232N-(1-(2-oxoethyl)-1H-pyrazol-4-yl)-5-(m-tolyl)oxazole-4-carboxamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

To N-(1-(2,2-dimethoxyethyl)-1H-pyrazol-4-yl)-5-(m-tolyl)oxazole-4-carboxamide (800 mg, 2.25 mmol) in THF (11.5 mL), 2 N aq. HCl-solution (10.3 mL, 20.60 mmol) was added dropwise and the resulting solution was refluxed (80° C.) for 1.5 h. The reaction mixture was allowed to reach rt, then neutralized with sat. aq. NaHCO3-solution and the org. solvent was removed under reduced pressure. The remaining aq. layer was extracted with EtOAc (2×) and the combined org. layer were washed with brine, dried (MgSO4), filtered and concentrated to obtain the title compound as a yellow solid which was used immediately in the next step. LC-MS conditions C: tR=0.72 min, [M+H2O+H]+=329.09.

후처리

  1. customto reach rt
  2. customsolvent was removed under reduced pressure
  3. extractionThe remaining aq. layer was extracted with EtOAc (2×)
  4. washlayer were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c22a4353ed574bde9b528ce25ba8b965
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09303023B2

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