proline dl-form → HCID 59540709, compound

HRID 1677413Notes

Reaction equation

HRID 1677413 reaction equation
[NH:1]1CC[CH2:6][CH:2]1[C:3](O)=O.C(=O)([O-])[O-].[K+].[K+].I[C:16]1[CH:17]=[C:18]([C:22]2[N:23]=[C:24]3[C:30]([C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:29][NH:28][C:25]3=[N:26][CH:27]=2)[CH:19]=[CH:20][CH:21]=1.C(N)(C)C>[Cu](I)I.CS(C)=O>[CH:2]([NH:1][C:16]1[CH:17]=[C:18]([C:22]2[N:23]=[C:24]3[C:30]([C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:29][NH:28][C:25]3=[N:26][CH:27]=2)[CH:19]=[CH:20][CH:21]=1)([CH3:6])[CH3:3]

Participants

7

Reactant 4

HCID 614proline dl-formHCID 6363IsopropylamineHCID 11430Potassium CarbonateHCID 59540678HCID 59540678, compound

Product 1

HCID 59540709HCID 59540709, compoundYield 16.5%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

DMSO (1.5 mL) was added to a mixture of copper iodide (10.6 mg; 0.056 mmol), d,l-proline (12.8 mg; 0.11 mmol), potassium carbonate (113 mg; 0.81 mmol), and 1-[2-(3-Iodo-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (150 mg; 0.37 mmol). Isopropyl amine (0.315 mL; 0.219 g, 3.7 mmol) was added and the resulting mixture was stirred at 110° C. (oil bath) for 24 hrs. The reaction mixture was quenched with water and extracted 3 times with EtOAc. The organic layers were combined, washed with brine, dried over MgSO4, and concentrated to give a yellow oil. Preparative HPLC afforded 6.1 mg (5% yield) of 1-[2-(3-Isopropylamino-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a yellow solid

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted 3 times with EtOAc
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give a yellow oil

Sources & evidence

ORD record
ord-41de820055c94c7cb3b14ce7330f46d0
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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