Imidazole → HCID 25168279, compound

HRID 1921963Notes

Reaction equation

HRID 1921963 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH:5]=[C:6]2[C:14]=1[O:13][C:9]1([CH2:12][CH2:11][CH2:10]1)[CH2:8][C@@H:7]2[NH:15][CH2:16][C@H:17]([C@@H:19]([NH:23][C:24](=[O:28])[CH2:25][O:26][CH3:27])[CH2:20][CH:21]=[CH2:22])[OH:18].C(=O)([O-])[O-].[Cs+].[Cs+].[NH:40]1[CH:44]=[CH:43][N:42]=[CH:41]1.CNCCNC>CN(C=O)C.[Cu]I.CN(C=O)C.O>[CH3:32][C:30]([CH3:31])([CH3:33])[CH2:29][C:4]1[CH:5]=[C:6]2[C:14](=[C:2]([N:40]3[CH:44]=[CH:43][N:42]=[CH:41]3)[CH:3]=1)[O:13][C:9]1([CH2:10][CH2:11][CH2:12]1)[CH2:8][C@@H:7]2[NH:15][CH2:16][C@H:17]([C@@H:19]([NH:23][C:24](=[O:28])[CH2:25][O:26][CH3:27])[CH2:20][CH:21]=[CH2:22])[OH:18]

Participants

8

Reactant 4

HCID 795ImidazoleHCID 8070N,N'-DimethylethylenediamineHCID 10796Cesium carbonateHCID 57515883HCID 57515883, compound

Product 1

HCID 25168279HCID 25168279, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Conditions

Temperature
185 °C

Procedure

To a microwave vial is added N-((1S)-1-((1R)-2-(((4S)-8-bromo-6-(2,2-dimethylpropyl)-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-4-yl)amino)-1-hydroxyethyl)-3-buten-1-yl)-2-methoxyacetamide (100 mg, 191 μmol), cesium carbonate (311 mg, 955 μmol), 1H-imidazole (65 mg, 955 μmol), and copper(I) iodide (36 mg, 191 μmol). The vial was purged with N2 5×, then 10:1 DMF/H2O (2 mL) and N1,N2-dimethylethane-1,2-diamine (21 μl, 191 μmol) were added. The vial was sealed and heated in a microwave at 185° C. for 30 min. The crude product was dissolved in DMF, filtered through an Acrodisc filter and purified by reverse phase HPLC to afford the title compound as a white amorphous solid. MS m/z=511.4 [M+H]+.

Workup

  1. customThe vial was purged with N2 5×
  2. customThe vial was sealed
  3. filtrationfiltered through an Acrodisc
  4. filtrationfilter
  5. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-35bb73ae5e364595b3b7af39c10ac377
Source dataset
uspto-grants-2012_05
Patent number
US08173810B2

Reaction notes

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