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

HRID 2196496

反応式

HRID 2196496 の反応式
[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

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 59843331HCID 59843331、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-676e7637187b4ee083cd4ee5d87678ef
出典データセット
uspto-grants-2012_12
特許番号
US08338437B2

関連ノート

読み込み中…