Hydrochloric Acid → HCID 67239540, compound

HRID 2363172Notes

Reaction equation

HRID 2363172 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]([NH:16][C:17]([C:19]2[N:20]=[C:21](Cl)[O:22][CH:23]=2)=[O:18])[CH3:15])[CH:5]=[C:6]([F:13])[C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10].[CH3:25][N:26]([CH3:36])[C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)C.C(COC)OC>[F:1][C:2]1[CH:3]=[C:4]([CH:14]([NH:16][C:17]([C:19]2[N:20]=[C:21]([C:31]3[CH:30]=[CH:29][CH:28]=[C:27]([N:26]([CH3:36])[CH3:25])[CH:32]=3)[O:22][CH:23]=2)=[O:18])[CH3:15])[CH:5]=[C:6]([F:13])[C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 27625273-(Dimethylamino)benzeneboronic acidHCID 671108872-Chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide

Product 1

HCID 67239540HCID 67239540, compoundYield 16.6%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
140 °C

Procedure

In a 5 ml glass tube were placed 2-chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide (50 mg, 0.13 mmol), 3-dimethylaminophenyl boronic acid (60 mg, 0.30 mmol), Cs2CO3 (129 mg, 0.40 mmol), Pd(PPh3)2Cl2(7 mg, 0.01 mmol), dimethoxyethane (0.8 mL), ethanol (0.2 mL), and a magnetic stir bar. The mixture was stirred at 140° C. for 20 minutes under microwave irradiation, acidified with 3N HCl, and extracted twice with EtOAc. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was triturated with ether to give title compound (10 mg, 16%).

Workup

  1. customIn a 5 ml glass tube were placed
  2. extractionextracted twice with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was triturated with ether

Sources & evidence

ORD record
ord-59c23e7611524050ad441f876a4d4e19
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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