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Sodium Hydroxide → (R)-5-(2-(5-fluoro-2-methoxyphenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

HRID 1631298
ノート
印刷プレビュー

反応式

HRID 1631298 の反応式
Cl[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([O:13]CC)=[O:12])=[C:4]2[N:3]=1.Cl.[F:17][C:18]1[CH:19]=[CH:20][C:21]([O:29][CH3:30])=[C:22]([C@H:24]2[CH2:28][CH2:27][CH2:26][NH:25]2)[CH:23]=1.C(N(C(C)C)CC)(C)C.[OH-].[Na+]>C(O)(C)C.CO>[F:17][C:18]1[CH:19]=[CH:20][C:21]([O:29][CH3:30])=[C:22]([C@H:24]2[CH2:28][CH2:27][CH2:26][N:25]2[C:2]2[CH:7]=[CH:6][N:5]3[N:8]=[CH:9][C:10]([C:11]([OH:13])=[O:12])=[C:4]3[N:3]=2)[CH:23]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 58063474Ethyl 5-chloropyrazolo(1,5-a)pyrimidine-3-carboxylateHCID 66519187(R)-2-(5-fluoro-2-methoxyphenyl)pyrrolidine hydrochloride

生成物 1

HCID 66847828(R)-5-(2-(5-fluoro-2-methoxyphenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid収率 32.2%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 3776Isopropanol溶媒

反応条件

温度
160 °C

実験手順

In a sealed tube, ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate (Preparation B, 500 mg, 2.22 mmol), (R)-2-(5-fluoro-2-methoxyphenyl)pyrrolidine hydrochloride salt (513 mg, 2.22 mmol), and diisopropylethylamine (0.774 mL, 4.43 mmol) were combined in isopropanol (2 mL) and heated at 160° C. for 3 days. 2N NaOH (6 mL) and MeOH (5 mL) were added and the reaction mixture stirred at ambient temperature for 24 hours, followed by heating to 40° C. for 3 hours. The reaction was partially concentrated, treated with saturated aqueous NH4Cl (10 mL) and the mixture extracted with EtOAc. The combined organic extracts were filtered, concentrated and the residue purified by reverse phase chromatography eluting with 0-60% acetonitrile/water to yield the title compound as a pink solid (254 mg, 32.2% yield). MS (apci) m/z=357.0 (M+H).

後処理

  1. temperatureby heating to 40° C. for 3 hours
  2. concentrationThe reaction was partially concentrated
  3. additiontreated with saturated aqueous NH4Cl (10 mL)
  4. extractionthe mixture extracted with EtOAc
  5. filtrationThe combined organic extracts were filtered
  6. concentrationconcentrated
  7. customthe residue purified by reverse phase chromatography
  8. washeluting with 0-60% acetonitrile/water

出典と根拠

ORDレコード
ord-793fbbfcbde7495497ed75e320835a19
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08791123B2

反応ノート

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