Sodium Bicarbonate → HCID 60172574, compound

HRID 2401288Notes

Reaction equation

HRID 2401288 reaction equation
[O:1]=[C:2]1[NH:6][CH2:5][C@H:4]([CH2:7][CH2:8][CH3:9])[N:3]1[CH2:10][C:11]([NH:13][C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][N:15]=1)=[O:12].Cl[C:25]1[N:30]=[CH:29][C:28]([F:31])=[CH:27][N:26]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC(C)([O-])C.[Na+].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:31][C:28]1[CH:27]=[N:26][C:25]([N:6]2[CH2:5][C@H:4]([CH2:7][CH2:8][CH3:9])[N:3]([CH2:10][C:11]([NH:13][C:14]3[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][N:15]=3)=[O:12])[C:2]2=[O:1])=[N:30][CH:29]=1

Participants

8

Reactant 5

HCID 516892Sodium BicarbonateHCID 5834662-Chloro-5-fluoropyrimidineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 86705171HCID 86705171, compound

Product 1

HCID 60172574HCID 60172574, compoundYield 29.9%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A solution of 2-[(5S)-2-oxo-5-propylimidazolidin-1-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]acetamide (70 mg), 2-chloro-5-fluoropyrimidine (33 mg), Pd2(dba)3 (22 mg), Xantphos (24 mg), and sodium tert-butoxide (30 mg) in toluene was stirred at 80° C. for 2 hr. Saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with ethyl acetate and drying over anhydrous magnesium sulfate. The desiccant was filtered off, the solvent was distilled off under reduced pressure, and the residue was purified by preparative HPLC to afford the title compound (27 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialdrying over anhydrous magnesium sulfate
  3. filtrationThe desiccant was filtered off
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-27b5fb073cb046f4b203dc4d2bde72a4
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

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