Trifluoroacetic acid methylene chloride → 3-(4-amino-3-methoxyphenyl)-1-(1-methyl-4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 897960

반응식

HRID 897960 반응식
FC(F)(F)C(O)=O.ClCCl.[NH2:11][C:12]1[N:17]=[CH:16][N:15]=[C:14]2[N:18]([CH:37]3[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]3)[N:19]=[C:20]([C:21]3[CH:26]=[CH:25][C:24]([NH:27]C(=O)OC(C)(C)C)=[C:23]([O:35][CH3:36])[CH:22]=3)[C:13]=12>ClCCl>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([C:20]2[C:13]3[C:14](=[N:15][CH:16]=[N:17][C:12]=3[NH2:11])[N:18]([CH:37]3[CH2:38][CH2:39][N:40]([CH3:43])[CH2:41][CH2:42]3)[N:19]=2)=[CH:22][C:23]=1[O:35][CH3:36]

참가 물질

4

반응물 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 22347171tert-butyl N-{4-[4-amino-1-(1-methyl-4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}carbamate

생성물 1

HCID 223470163-(4-amino-3-methoxyphenyl)-1-(1-methyl-4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine수율 95.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of trifluoroacetic acid/dichloromethane (20:80, 7 mL) was added to a solution of tert-butyl N-{4-[4-amino-1-(1-methyl-4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}carbamate (240 mg, 0.529 mmol) in dichloromethane (4 mL) at 0° C. 15 minutes later, the ice-bath was removed and the reaction mixture was stirred at room temperature for 4 hours. The solvents were evaporated and the residue was dissolved in dichloromethane. Sodium hydroxide (1.0N) was added to adjust the pH to about 10. The layers were separated and the aqueous layer was extracted with dichloromethane four times. The combined organic layer was washed with brine, dried over MgSO4, filtered and evaporated to give 3-(4-amino-3-methoxyphenyl)-1-(1-methyl-4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (178 mg, 95%). HPLC (Waters 486-Column: delta pak, C18, 5 um, 300 Å, 150×3.9 mm. Eluents: 5% B/A to 95% B/A in 10 min. (B: acetonitrile, A: 50 mM ammonia acetate buffer, pH 4.5), 1.0 mL/min.) Rt=6.45 min.

후처리

  1. custom15 minutes later, the ice-bath was removed
  2. customThe solvents were evaporated
  3. dissolutionthe residue was dissolved in dichloromethane
  4. additionSodium hydroxide (1.0N) was added
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with dichloromethane four times
  7. washThe combined organic layer was washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated

출처 및 근거

ORD 기록
ord-b60c97f5e9754088abd5db707462823c
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06921763B2

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