Methanol → HCID 89691440, compound

HRID 2202845Notes

Reaction equation

HRID 2202845 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[N:13]=[CH:12][NH:11][C:10](=[O:14])[CH:9]=2)=[CH:4][CH:3]=1.[CH:17]1([C:20]2[N:21]=[C:22]3[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][N:23]3[C:31]=2[CH3:32])[CH2:19][CH2:18]1.C(Cl)Cl.CO>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][C:8]2[N:13]=[CH:12][N:11]([C:25]3[CH:26]=[CH:27][C:22]4[N:23]([C:31]([CH3:32])=[C:20]([CH:17]5[CH2:19][CH2:18]5)[N:21]=4)[CH:24]=3)[C:10](=[O:14])[CH:9]=2)=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 89690253HCID 89690253, compoundHCID 89690439HCID 89690439, compound

Product 1

HCID 89691440HCID 89691440, compoundYield 5.8%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 1049PyridineSolvent

Procedure

To a mixture of 6-((4-chlorobenzyl)oxy)pyrimidin-4(3H)-one (150 mg), (2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)boronic acid (275 mg), DCM (15 ml) and MeOH (15 ml) were added copper acetate (346 mg) and pyridine (0.5 ml), and the resulting reaction mixture was stirred at room temperature for 16 h. The solids were then filtered through Celite, and the filtrate was poured into 1 M HCl. The mixture was extracted with DCM, and the combined DCM layer was washed successively with saturated NaHCO3 solution, brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by preparative HPLC to give the title compound (15 mg) as an off-white solid.

Workup

  1. customthe resulting reaction mixture
  2. filtrationThe solids were then filtered through Celite
  3. additionthe filtrate was poured into 1 M HCl
  4. extractionThe mixture was extracted with DCM
  5. washthe combined DCM layer was washed successively with saturated NaHCO3 solution, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-8bf80e99cfa84005a7301c6323d639e9
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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