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

HRID 1852991

反応式

HRID 1852991 の反応式
[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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-34abecc001b34bfab6edcb8d7bb7f0f4
出典データセット
uspto-grants-2015_02
特許番号
US08962596B2

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