Water → 5-(1-aminoethyl)-3-(6-fluoroquinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine

HRID 2369020노트

반응식

HRID 2369020 반응식
[N:1]([CH:4]([C:6]1[CH:11]=[C:10]([N:12]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:9]2[N:29]=[CH:30][C:31]([C:32]3[CH:33]=[N:34][C:35]4[C:40]([CH:41]=3)=[CH:39][C:38]([F:42])=[CH:37][CH:36]=4)=[C:8]2[N:7]=1)[CH3:5])=[N+]=[N-].C1COCC1.CP(C)C.O>CCOC(C)=O>[NH2:1][CH:4]([C:6]1[CH:11]=[C:10]([N:12]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:18])([CH3:19])[CH3:20])[N:9]2[N:29]=[CH:30][C:31]([C:32]3[CH:33]=[N:34][C:35]4[C:40]([CH:41]=3)=[CH:39][C:38]([F:42])=[CH:37][CH:36]=4)=[C:8]2[N:7]=1)[CH3:5]

참가 물질

6

반응물 4

HCID 962WaterHCID 8028Tetrahydrofuran2회HCID 68983TrimethylphosphineHCID 86664796HCID 86664796, 화합물

생성물 1

HCID 665845645-(1-aminoethyl)-3-(6-fluoroquinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine수율 82%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 5-(1-azidoethyl)-3-(6-fluoroquinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (6.2 g, 10.3 mmol) and THF (90 mL) was added 1M trimethylphosphine in THF (30.8 mL, 30.8 mmol) dropwise. After 30 minutes the reaction was complete by HPLC. Water (30 mL) was therefore added and the reaction stirred an additional hour. The contents of the flask were transferred to a separatory funnel, diluted with 300 mL of EtOAc and washed three times with water and three times with brine. The organics were dried over sodium sulfate, filtered and concentrated in vacuo. Purified the remaining crude material by flash chromatography (0-2% 0.7N NH3 in MeOH/CHCl3) to afford 5-(1-aminoethyl)-3-(6-fluoroquinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (4.9 g, 82% yield) as a yellow solid. HPLC: 6.62 min (Method C). LCMS:ESI+ m/z of 583 (M+H)

후처리

  1. customThe contents of the flask were transferred to a separatory funnel
  2. washwashed three times with water and three times with brine
  3. dry with materialThe organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurified the remaining crude material by flash chromatography (0-2% 0.7N NH3 in MeOH/CHCl3)

출처 및 근거

ORD 기록
ord-34d5981ed57d410eb1dbfdb892f6bf3d
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703784B2

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