Imidazole → HCID 57581529, compound

HRID 1689975Notes

Reaction equation

HRID 1689975 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:19])[C@@H:14]([CH3:26])[CH2:13]2)=[N:4][N:3]=1.[NH:27]1[CH:31]=[CH:30][N:29]=[CH:28]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu]I.O1CCOCC1>[N:27]1([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[O:19])[C@@H:14]([CH3:26])[CH2:13]3)=[N:4][N:3]=2)[CH:31]=[CH:30][N:29]=[CH:28]1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 62657Potassium Phosphate, TribasicHCID 57581500HCID 57581500, compound

Product 1

HCID 57581529HCID 57581529, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

Compound 77 was prepared as described in general Method I. A 15 mL Schlenk tube was charged with (S)-(4-(4-chlorophthalazin-1-yl)-2-methylpiperazin-1-yl)(phenyl)methanone JK-4 (100 mg, 0.273 mmol), 1H-imidazole (22.3 mg, 0.328 mmol), copper (I) iodide (2.6 mg, 0.0136 mmol), potassium phosphate (122 mg, 0.573 mmol), trans-cyclohexanediamine (3.3 μl, 0.0273 mmol), and dioxane (0.75 mL). The vessel was evacuated, backfilled with argon 5 times, and then heated at 110° C. for 22 hours. After cooling, the reaction was then taken up in ethyl acetate (80 mL) and washed with aqueous K2CO3 (10%), water, and saturated sodium chloride. The organics were dried (MgSO4) and evaporated to give a yellow oil. Chromatography over silica gel with a gradient of hexanes/0-100% ethyl acetate gave a white solid, compound 77. MS (M+H)+=399.2.

Workup

  1. customCompound 77 was prepared
  2. customThe vessel was evacuated
  3. temperatureAfter cooling
  4. washwashed with aqueous K2CO3 (10%), water, and saturated sodium chloride
  5. dry with materialThe organics were dried (MgSO4)
  6. customevaporated
  7. customto give a yellow oil

Sources & evidence

ORD record
ord-7fd6f7ff7357420f8efd64f3d6733031
Source dataset
uspto-grants-2012_04
Patent number
US08153633B2

Reaction notes

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