Trifluoroacetic acid → {3-[6-(3-chloro-benzylamino)-pyridin-2-yl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}-(2-morpholin-4-yl-ethyl)-amine

HRID 1809718ノート

反応式

HRID 1809718 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:39]=[CH:40][CH:41]=1)[CH2:5][NH:6][C:7]1[N:12]=[C:11]([C:13]2[C:21]3[C:16](=[N:17][C:18]([NH:22][CH2:23][CH2:24][N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[N:19][CH:20]=3)[N:15](COCC[Si](C)(C)C)[N:14]=2)[CH:10]=[CH:9][CH:8]=1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:39]=[CH:40][CH:41]=1)[CH2:5][NH:6][C:7]1[N:12]=[C:11]([C:13]2[C:21]3[C:16](=[N:17][C:18]([NH:22][CH2:23][CH2:24][N:25]4[CH2:26][CH2:27][O:28][CH2:29][CH2:30]4)=[N:19][CH:20]=3)[NH:15][N:14]=2)[CH:10]=[CH:9][CH:8]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68108833HCID 68108833、化合物

生成物 1

HCID 178478111{3-[6-(3-chloro-benzylamino)-pyridin-2-yl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}-(2-morpholin-4-yl-ethyl)-amine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of [3-[6-(3-chloro-benzylamino)-pyridin-2-yl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-morpholin-4-yl-ethyl)-amine (110 mg, 0.185 mmol) in dichloromethane (2.5 mL) was added TFA (2.5 mL). The reaction mixture was stirred for 2 hours at room temperature. The pH of the mixture was adjusted to about 8 with saturated NaHCO3 solution. The resulting mixture was extracted with ethyl acetate. The organic layer was dried and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, dichloromethane:MeOH, 20:1), then further purified by prep-HPLC to give {3-[6-(3-chloro-benzylamino)-pyridin-2-yl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}-(2-morpholin-4-yl-ethyl)-amine. (Yield 23 mg, 26%).

後処理

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. customThe organic layer was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography (silica gel, dichloromethane:MeOH, 20:1)
  5. customfurther purified by prep-HPLC

出典と根拠

ORDレコード
ord-daa07fe3b0464c7195a201aa0d669bf3
出典データセット
uspto-grants-2013_01
特許番号
US08362023B2

反応ノート

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