Hydrochloric Acid → (4-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)thiophen-2-yl)methanamine

HRID 2196496

반응식

HRID 2196496 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[CH:12]=[C:13]([C:16]([NH2:18])=O)[S:14][CH:15]=2)[N:9]=[C:8]([C:19]([F:22])([F:21])[F:20])[CH:7]=1.Cl>C1COCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[CH:12]=[C:13]([CH2:16][NH2:18])[S:14][CH:15]=2)[N:9]=[C:8]([C:19]([F:21])([F:22])[F:20])[CH:7]=1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 59843331HCID 59843331, 화합물

생성물 1

HCID 59843286(4-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)thiophen-2-yl)methanamine수율 90%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
70 °C

실험 절차

A one molar solution of BH3 in THF (1.2 mL, 1.2 mmol) was added to amide 4 (128 mg, 0.39 mmol) in THF (1.5 mL) and the mixture was heated in a sealed tube at 70° C. for 5 h, then it was stirred at room temperature for 16 h. The mixture was cooled in ice and few drops of conc HCl were added, then most of the solvent was removed and H2O was added and the mixture was heated to reflux for 20 min. EtOAc was added and the PH adjusted to 8 with saturated NaHCO3 and extracted with EtOAc (2×). The organic extracts were dried over MgSO4, filtered and concentrated leaving crude 5 (110 mg) as a clear oil. LRMS (ESI): calc. 313.3; found 314.0 (MH)+. The material was used as is for the next step.

후처리

  1. temperatureThe mixture was cooled in ice
  2. custommost of the solvent was removed
  3. additionH2O was added
  4. temperaturethe mixture was heated
  5. temperatureto reflux for 20 min
  6. additionEtOAc was added
  7. extractionextracted with EtOAc (2×)
  8. dry with materialThe organic extracts were dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-676e7637187b4ee083cd4ee5d87678ef
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338437B2

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