Sodium hydride → HCID 86695246, 화합물

HRID 1504082노트

반응식

HRID 1504082 반응식
[N:1]1([CH:7]2[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[C:17]1[C:18]2[CH:25]=[C:24]([CH2:26][CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[S:23][C:19]=2[N:20]=[CH:21][N:22]=1>C1COCC1>[N:1]1([CH:7]2[CH2:8][CH2:9][CH:10]([O:13][C:17]3[C:18]4[CH:25]=[C:24]([CH2:26][CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:32])[CH3:34])[S:23][C:19]=4[N:20]=[CH:21][N:22]=3)[CH2:11][CH2:12]2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 582055574-(Morpholin-4-yl)cyclohexan-1-olHCID 86695235HCID 86695235, 화합물

생성물 1

HCID 86695246HCID 86695246, 화합물수율 39.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 4-(morpholin-4-yl)cyclohexan-1-ol (143 mg, 0.77 mmol, 1.10 equiv) in THF (20 mL) was added sodium hydride (140 mg, 3.50 mmol, 5.00 equiv, 60% dispersion in mineral oil) at 0° C. The solution was stirred for 30 min at room temperature under nitrogen. Then tert-butyl N-(2-[4-chlorothieno[2,3-d]pyrimidin-6-yl]ethyl)carbamate (220 mg, 0.70 mmol, 1.00 equiv) in 5 mL of THF was added via syringe and the resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of brine and extracted with EtOAc. The organic layers were combined and dried over anhydrous sodium sulfate. After filtration and concentration in vacuo, the residue was purified by a silica gel column with DCM/MeOH (30:1-10:1) to provide 127 mg (39%) of tert-butyl N-[2-(4-[[4-(morpholin-4-yl)cyclohexyl]oxy]thieno[2,3-d]pyrimidin-6-yl)ethyl]carbamate as a white solid. MS (ES): m/z 463 (M+H)+.

후처리

  1. stirringthe resulting solution was stirred overnight at room temperature
  2. customThe reaction was then quenched by the addition of brine
  3. extractionextracted with EtOAc
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration and concentration in vacuo
  6. customthe residue was purified by a silica gel column with DCM/MeOH (30:1-10:1)

출처 및 근거

ORD 기록
ord-ef0e4af8081840f88648a81d6500de35
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212190B2

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