Hydrochloric Acid → HCID 68182480, compound

HRID 1623906Notes

Reaction equation

HRID 1623906 reaction equation
[F-].[K+].C[Si](C)(C)[C:5]([F:8])([F:7])[F:6].Br[C:12]1[N:13]=[CH:14][C:15]([N:18]2[C:25]3[C@@H:24]4[CH2:26][C@@H:23]4[CH2:22][C:21]=3[C:20]([C:27]([OH:29])=[O:28])=[N:19]2)=[N:16][CH:17]=1.Cl>[Cu]I.CCOC(C)=O.CN1CCCC1=O>[F:6][C:5]([F:8])([F:7])[C:12]1[N:13]=[CH:14][C:15]([N:18]2[C:25]3[C@@H:24]4[CH2:26][C@@H:23]4[CH2:22][C:21]=3[C:20]([C:27]([OH:29])=[O:28])=[N:19]2)=[N:16][CH:17]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 522689Potassium FluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 86669650HCID 86669650, compound

Product 1

HCID 68182480HCID 68182480, compoundYield 16.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
50 °C

Procedure

In an oven-dried 20 mL scintillation vial were placed potassium fluoride (523 mg, 9.00 mmol) and copper (I) iodide (1714 mg, 9.00 mmol). N-Methyl-2-pyrrolidinone (10 mL) was added to the mixture followed by trimethyl(trifluoromethyl)silane (2.66 mL, 18.00 mmol). The reaction was stirred at 50° C. for 1 h. (1aR,5aR)-2-(5-Bromopyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid (289 mg, 0.900 mmol) (from Example 1.13, Step B) was then added. The brown mixture was stirred at 50° C. for 17 h before poured into 1 M HCl (75 mL). EtOAc (50 mL) were added and the mixture was stirred vigorously for 5 minutes. The mixture was filtered and the layers were separated. The aqueous layer was extracted with EtOAc (50 mL). The combined organic layers were concentrated and the residue was purified by preparative HPLC to give the title compound as a yellow solid (45 mg). LCMS m/z=311.2 [M+H]+.

Workup

  1. additionwas then added
  2. stirringthe mixture was stirred vigorously for 5 minutes
  3. filtrationThe mixture was filtered
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with EtOAc (50 mL)
  6. concentrationThe combined organic layers were concentrated
  7. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-edabe30c39134241bde1d84a40e477e6
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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