Trifluoroacetic acid → 3-(4-(7-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-3-cyclopropylpropanenitrile

HRID 1852991

반응식

HRID 1852991 반응식
[CH:1]1([CH:4]([N:8]2[CH:12]=[C:11]([C:13]3[N:18]4[CH:19]=[CH:20][N:21]=[C:17]4[CH:16]=[C:15]([C:22]4[CH:23]=[N:24][N:25](COCC[Si](C)(C)C)[CH:26]=4)[N:14]=3)[CH:10]=[N:9]2)[CH2:5][C:6]#[N:7])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH:25]1[CH:26]=[C:22]([C:15]2[N:14]=[C:13]([C:11]3[CH:10]=[N:9][N:8]([CH:4]([CH:1]4[CH2:3][CH2:2]4)[CH2:5][C:6]#[N:7])[CH:12]=3)[N:18]3[CH:19]=[CH:20][N:21]=[C:17]3[CH:16]=2)[CH:23]=[N:24]1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 674584153-cyclopropyl-3-(4-(7-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile

생성물 1

HCID 674589353-(4-(7-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-3-cyclopropylpropanenitrile수율 98%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 3-cyclopropyl-3-(4-(7-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile (Example 32, 65.0 mg, 0.137 mmol) in DCM (2 mL) was added trifluoroacetic acid (2 mL) and the mixture was stirred at ambient temperature for 1.5 hours. The mixture was concentrated and the residue was partitioned into EtOAc (3 mL) and saturated NaHCO3 (3 mL). The biphasic mixture was stirred for 15 minutes and NaCl was added until saturated. The EtOAc layer was removed and the remaining aqueous portion was extracted with EtOAc. The combined EtOAc extracts were dried over MgSO4, filtered through a Celite plug and concentrated. The residual solid was dissolved in 10% MeOH/EtOAc and eluted through a SiO2 column using 10% MeOH/EtOAc for elution. The solution was concentrated to give the title compound (46 mg, 98% yield) as a white solid. MS (apci) m/z=345.2 (M+H).

후처리

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned into EtOAc (3 mL) and saturated NaHCO3 (3 mL)
  3. stirringThe biphasic mixture was stirred for 15 minutes
  4. additionNaCl was added until saturated
  5. customThe EtOAc layer was removed
  6. extractionthe remaining aqueous portion was extracted with EtOAc
  7. dry with materialThe combined EtOAc extracts were dried over MgSO4
  8. filtrationfiltered through a Celite plug
  9. concentrationconcentrated
  10. dissolutionThe residual solid was dissolved in 10% MeOH/EtOAc
  11. washeluted through a SiO2 column
  12. washfor elution
  13. concentrationThe solution was concentrated

출처 및 근거

ORD 기록
ord-34abecc001b34bfab6edcb8d7bb7f0f4
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962596B2

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