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 1809718노트

반응식

HRID 1809718 반응식
[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

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68108833HCID 68108833, 화합물

생성물 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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-daa07fe3b0464c7195a201aa0d669bf3
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362023B2

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