Triethylamine → {4-[3-(3-bromo-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester

HRID 1809707노트

반응식

HRID 1809707 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[N:12][C:13](Cl)=[N:14][CH:15]=3)[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.CCN(CC)CC.Cl[CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31].[C:34]([NH:41][C@H:42]1[CH2:47][CH2:46][C@H:45]([NH2:48])[CH2:44][CH2:43]1)([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35]>CN(C=O)C.O>[C:37]([O:36][C:34](=[O:35])[NH:41][CH:42]1[CH2:43][CH2:44][CH:45]([NH:48][C:13]2[N:12]=[C:11]3[N:10]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[N:9]=[C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=4)[C:16]3=[CH:15][N:14]=2)[CH2:46][CH2:47]1)([CH3:40])([CH3:38])[CH3:39]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178419079HCID 178419079, 화합물HCID 178478326HCID 178478326, 화합물

생성물 1

HCID 68108922{4-[3-(3-bromo-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-(3-bromo-phenyl)-6-chloro-1H-pyrazolo[3,4-d]pyrimidine (from Example 38 supra) (3.0 g, 9.7 mmol), Et3N (5.4 mL, 38.8 mmol) in DMF (50 mL), (2-(chloromethoxy)-ethyl)trimethylsilane (SEM-Cl, 2.0 mL, 11.6 mmol) was added in one portion. The resultant mixture was stirred for 30 minutes at room temperature. To this solution, N-Boc-trans-1,4-cyclohexanediamine (2.48 g, 11.6 mmol) was added. The resulting mixture was stirred for one hour at room temperature. The reaction was then poured into water (200 mL) and extracted with EtOAc (3×200 mL). The EtOAc extract was dried over Na2SO4, filtered and concentrated. The crude product was purified by chromatography (silica gel, 200-300 mesh, EtOAc) to give {4-[3-(3-bromo-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester as yellow oil. (Yield 2.2 g, 37.3%).

후처리

  1. extractionextracted with EtOAc (3×200 mL)
  2. extractionThe EtOAc extract
  3. dry with materialwas dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by chromatography (silica gel, 200-300 mesh, EtOAc)

출처 및 근거

ORD 기록
ord-92e877238aa44ff8af98d3ec62cd6413
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362023B2

반응 노트

불러오는 중…