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

HRID 432417

반응식

HRID 432417 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]([CH:43]4[CH2:48][CH2:47][N:46]([CH3:49])[CH2:45][CH2:44]4)[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[CH2:42][CH2:41][N:40]([CH:43]4[CH2:48][CH2:47][N:46]([CH3:49])[CH2:45][CH2:44]4)[CH2:39][CH2:38]3)[N:19]=2)=[CH:22][C:23]=1[O:35][CH3:36]

참가 물질

4

반응물 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 22347076tert-butyl N-{4-[4-amino-1-[1-(1-methylpiperidin-4-yl)-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}carbamate

생성물 1

HCID 223469753-(4-amino-3-methoxyphenyl)-1-[1-(1-methylpiperidin-4-yl)piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine수율 97.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of trifluoroacetic acid/dichloromethane (20:80, 28 mL) was added to a solution of tert-butyl N-{4-[4-amino-1-[1-(1-methylpiperidin-4-yl)-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}carbamate (0.914 g, 1.70 mmol) in dichloromethane (5 mL) at 0° C. After 15 minutes, the ice-bath was removed and the reaction mixture was stirred at room temperature for 5 hours. Solvents were then evaporated and the residue was dissolved in dichloromethane. Saturated sodium bicarbonate was added to adjust the pH to about 8. The layers were separated and the aqueous layer was extracted with dichloromethane. The combined organic layer was washed with brine, dried over MgSO4, filtered and evaporated give 3-(4-amino-3-methoxyphenyl)-1-[1-(1-methylpiperidin-4-yl)-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.726 g, 97%). 1H NMR (CDCl3) δ 1.67 (m, 2H) 1.83 (m, 4H), 2.00 (m, 2H), 2.27 (s, 3H), 2.39 (m, 5H), 2.91 (m, 2H), 3.08 (m, 2H), 3.92 (s, 3H), 3.99 (m, 2 h), 4.73 (m, 1H), 5.56 (bs, 2H), 6.82 (d, J=7.87, 1H), 7.08 (d, J=7.84, 1H), 7.13 (s, 1H), 8.34 (s, 1H).

후처리

  1. customthe ice-bath was removed
  2. customSolvents were then evaporated
  3. dissolutionthe residue was dissolved in dichloromethane
  4. additionSaturated sodium bicarbonate was added
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with dichloromethane
  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-f3dd1f3084a2406b9ff40057af7bae86
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660744B1

연결된 노트

불러오는 중…