Sodium Carbonate → HCID 58485287, compound

HRID 1046264Notes

Reaction equation

HRID 1046264 reaction equation
C([O-])([O-])=O.[Na+].[Na+].C[O:8][C:9]([C:11]1[N:12]=[N:13][C:14](Cl)=[CH:15][CH:16]=1)=[O:10].[OH:18][C:19]([CH3:52])([CH3:51])[CH2:20][C@@:21]1([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[O:26][C:25](=[O:27])[N:24]([C@H:28]([C:30]2[CH:35]=[CH:34][C:33](B3OC(C)(C)C(C)(C)O3)=[CH:32][CH:31]=2)[CH3:29])[CH2:23][CH2:22]1>CN(C)C=O>[OH:18][C:19]([CH3:51])([CH3:52])[CH2:20][C@@:21]1([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[O:26][C:25](=[O:27])[N:24]([C@H:28]([C:30]2[CH:31]=[CH:32][C:33]([C:14]3[N:13]=[N:12][C:11]([C:9]([OH:8])=[O:10])=[CH:16][CH:15]=3)=[CH:34][CH:35]=2)[CH3:29])[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 12379801Methyl 6-chloropyridazine-3-carboxylateHCID 59532385(S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one

Product 1

HCID 58485287HCID 58485287, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2 M aqueous Na2CO3 solution (1.46 mL) was added to a mixture of 6-chloropyridazine-3-carboxylic acid methyl ester (0.38 g) and (S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-[(S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl]-1,3-oxazinan-2-one (0.70 g) in N,N-dimethylformamide (8 mL). The resulting mixture was sparged with argon for 10 min, before [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium(II) dichloromethane complex (72 mg) was added. The mixture was heated to 100° C. and stirred at this temperature overnight. After cooling the mixture to ambient temperature, water and 1 M hydrochloric acid were added and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine and dried (MgSO4). The solvent was evaporated and the residue was purified by HPLC on reversed phase (methanol/water/F3CCO2H) to afford the title compound as an oil that solidifies while standing. Yield: 0.36 g (52% of theory); Mass spectrum (ESI−): m/z=474 [M−H]−.

Workup

  1. customThe resulting mixture was sparged with argon for 10 min, before [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium(II) dichloromethane complex (72 mg)
  2. additionwas added
  3. temperatureAfter cooling the mixture to ambient temperature
  4. additionwater and 1 M hydrochloric acid were added
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. customThe solvent was evaporated
  9. customthe residue was purified by HPLC on reversed phase (methanol/water/F3CCO2H)

Sources & evidence

ORD record
ord-119b3f30031c433895b401a45ee1e2d9
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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