Potassium Acetate → 6-Methyl-4-[8-(4-morpholin-4-ylphenylamino)-imidazo[1,2-a]pyrazin-5-yl]-1H-pyridin-2-one

HRID 1924952노트

반응식

HRID 1924952 반응식
C(OC(=O)[N:7]([C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[CH:28][CH:27]=1)[C:8]1[C:9]2[N:10]([CH:23]=[CH:24][N:25]=2)[C:11](B2OC(C)(C)C(C)(C)O2)=[CH:12][N:13]=1)(C)(C)C.Br[C:40]1[CH:45]=[C:44]([CH3:46])[N:43]=[C:42]([O:47][Si](C(C)(C)C)(C)C)[CH:41]=1.CC([O-])=O.[K+]>O1CCOCC1>[CH3:46][C:44]1[NH:43][C:42](=[O:47])[CH:41]=[C:40]([C:11]2[N:10]3[CH:23]=[CH:24][N:25]=[C:9]3[C:8]([NH:7][C:26]3[CH:27]=[CH:28][C:29]([N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)=[CH:30][CH:31]=3)=[N:13][CH:12]=2)[CH:45]=1

참가 물질

5

반응물 3

HCID 517044Potassium AcetateHCID 58423078(4-Morpholin-4-ylphenyl)-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)imidazo[1,2-a]pyrazin-8-yl]carbamic acid tert-butyl esterHCID 590230434-Bromo-2-((tert-butyldimethylsilyl)oxy)-6-methylpyridine

생성물 1

HCID 590230826-Methyl-4-[8-(4-morpholin-4-ylphenylamino)-imidazo[1,2-a]pyrazin-5-yl]-1H-pyridin-2-one

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

Half of the solution prepared in Step 3 and 4-bromo-2-(tert-butyldimethylsilyloxy)-6-methylpyridine (30 mg, 0.10 mmol) are mixed and diluted with dioxane (0.15 mL). KOAc (15 mg, 0.15 mmol) and Pd(dppf)Cl2DCM (2 mg, 0.0025 mmol) are added and the system is flushed with N2 and heated at 80° C. for 2.5 h. The mixture is cooled to rt, diluted with DCM (5 mL) and MeOH (1 mL) and filtered through celite. The solvents are evaporated, the residue is suspended in DCM (2 mL) and TFA (0.5 mL) is added, causing the solid to dissolve. The solution is stirred at rt overnight and the solvents are then evaporated. The residue is purified by preparative HPLC to afford the title compound as a yellow solid. LCMS: Rt=0.84 min (100%), m/z (ESI) 403 (M+H)+.

후처리

  1. customthe system is flushed with N2
  2. temperatureThe mixture is cooled to rt
  3. additiondiluted with DCM (5 mL) and MeOH (1 mL)
  4. filtrationfiltered through celite
  5. customThe solvents are evaporated
  6. additionTFA (0.5 mL) is added
  7. dissolutionto dissolve
  8. customthe solvents are then evaporated
  9. customThe residue is purified by preparative HPLC

출처 및 근거

ORD 기록
ord-7276c5b3846b40519333be7bf89e2eb1
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178530B2

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