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

HRID 1366176Notes

Reaction equation

HRID 1366176 reaction equation
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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-eed3d1a61b274a4492ff4932ab4d9540
Source dataset
uspto-grants-2011_02
Patent number
US07893058B2

Reaction notes

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