Potassium Carbonate → 1-{2-Fluoro-4-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl}pyrrolidin-2-one

HRID 500196Notes

Reaction equation

HRID 500196 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]3[N:12]([C:14]([C:17]4([C:20]5[CH:21]=[C:22]6[C:27](=[CH:28][CH:29]=5)[N:26]=[CH:25][CH:24]=[CH:23]6)[CH2:19][CH2:18]4)=[CH:15][N:16]=3)[CH:13]=2)=[CH:4][C:3]=1[F:30].[NH:31]1[CH2:35][CH2:34][CH2:33][C:32]1=[O:36].CN[C@H]1CCCC[C@@H]1NC.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.[Cu]I>[F:30][C:3]1[CH:4]=[C:5]([C:8]2[CH:9]=[N:10][C:11]3[N:12]([C:14]([C:17]4([C:20]5[CH:21]=[C:22]6[C:27](=[CH:28][CH:29]=5)[N:26]=[CH:25][CH:24]=[CH:23]6)[CH2:19][CH2:18]4)=[CH:15][N:16]=3)[CH:13]=2)[CH:6]=[CH:7][C:2]=1[N:31]1[CH2:35][CH2:34][CH2:33][C:32]1=[O:36]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 120252-PyrrolidoneHCID 13822957(1S,2S)-(+)-N,N'-Dimethylcyclohexane-1,2-diamineHCID 672251686-{1-[6-(4-Bromo-3-fluorophenyl)imidazo[1,2-a]pyrimidin-3-yl]cyclopropyl}quinoline

Product 1

HCID 251453771-{2-Fluoro-4-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]phenyl}pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 6-{1-[6-(4-bromo-3-fluorophenyl)imidazo[1,2-a]pyrimidin-3-yl]cyclopropyl}quinoline (20 mg, 0.04 mmol) in 1,4-dioxane (1 mL) was added 2-pyrrolidinone (5.7 mg, 0.067 mmol), (1S,2S)—N,N′-dimethylcyclohexane-1,2-diamine (1 mg, 0.009 mmol), copper(I) iodide (0.8 mg, 0.004 mmol), and potassium carbonate (13 mg, 0.095 mmol). The mixture was irradiated at under microwave 150° C. for 1 h. After cooling to RT, the solution was purified by RP-HPLC (pH=10) to afford the desired compound. LCMS: (M+H)+=464.1.

Workup

  1. customThe mixture was irradiated at under microwave 150° C. for 1 h
  2. customthe solution was purified by RP-HPLC (pH=10)

Sources & evidence

ORD record
ord-1396b304841e44e29b12c79ef7463ead
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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