Acetic Acid → 4-(5-Amino-3-tert-butyl-pyrazol-1-yl)-benzoic acid

HRID 221860

반응식

HRID 221860 반응식
[CH3:1][C:2]([CH3:9])([CH3:8])[C:3](=O)[CH2:4][C:5]#[N:6].[NH:10]([C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1)[NH2:11].C(O)(=O)C>CCO.C1COCC1>[NH2:6][C:5]1[N:10]([C:12]2[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:19][CH:20]=2)[N:11]=[C:3]([C:2]([CH3:9])([CH3:8])[CH3:1])[CH:4]=1

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 120894-Hydrazinobenzoic acidHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-

생성물 1

HCID 9746884-(5-Amino-3-tert-butyl-pyrazol-1-yl)-benzoic acid수율 99%

시약·촉매·용매 1

HCID 21873804Tetrahydrofuran ethanol용매

실험 절차

A mixture of 4,4-dimethyl-3-oxo-pentanenitrile (4.52 g, 36.15 mmol), 4-hydrazinobenzoic acid (5.00 g, 32.86 mmol), and acetic acid (2 mL) in EtOH/THF (1:1) was refluxed for 16 h. After cooling, the solvent was concentrated at reduced pressure, and the crude was re-dissolved in EtOAc. The organic layer was washed with aqueous saturated Na2CO3 solution and brine, dried over MgSO4, filtered, and concentrated to half its volume. The resulting residue was filtered, and the solids were washed with cold EtOAc and dried under high vacuum to afford the title compound as a white solid (8.4 g, 99%). 1H-NMR (DMSO-d6) δ 12.91 (s, 1H), 7.99 (d, J=6.0 Hz, 2H), 7.75 (d, J=9.0 Hz, 2H), 5.42 (s, 1H), 5.39 (s, 2H), 1.21 (s, 9H); MS LC-MS [M+H]+=260, RT=1.83 min.

후처리

  1. temperaturewas refluxed for 16 h
  2. temperatureAfter cooling
  3. concentrationthe solvent was concentrated at reduced pressure
  4. dissolutionthe crude was re-dissolved in EtOAc
  5. washThe organic layer was washed with aqueous saturated Na2CO3 solution and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to half its volume
  9. filtrationThe resulting residue was filtered
  10. washthe solids were washed with cold EtOAc
  11. customdried under high vacuum

출처 및 근거

ORD 기록
ord-61257910ddf04c16842a9415e8734b1b
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207166B2

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