Trifluoroacetic acid → HCID 57522618, compound

HRID 1968528Notes

Reaction equation

HRID 1968528 reaction equation
[NH2:1][C@@H:2]1[C@@H:7]2[CH2:8][C@@H:4]([CH:5]=[CH:6]2)[C@@H:3]1[C:9]([NH2:11])=[O:10].FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+].[Cl:24][C:25]1[N:30]=[C:29](Cl)[C:28]([Cl:32])=[CH:27][N:26]=1>CO.O.O.C(OCC)(=O)C>[Cl:24][C:25]1[N:30]=[C:29]([NH:1][C@@H:2]2[C@@H:7]3[CH2:8][C@@H:4]([CH:5]=[CH:6]3)[C@@H:3]2[C:9]([NH2:11])=[O:10])[C:28]([Cl:32])=[CH:27][N:26]=1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 2372592,4,5-TrichloropyrimidineHCID 516892Sodium BicarbonateHCID 42580098105786-40-1

Product 1

HCID 57522618HCID 57522618, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

A light suspension of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide, trifluoroacetic acid (3 g, 11.27 mmol) and sodium bicarbonate (1.893 g, 22.54 mmol) in 39 ml of 2:1 methanol/water at room temperature was treated with 2,4,5-trichloropyrimidine (1.550 ml, 13.52 mmol). The resulting mixture was stirred at room temperature for 2 days, diluted with water (20 ml) and ethyl acetate (30 ml); the separated aqueous phase was extracted with ethyl acetate (4×20 ml) and the combined organic layers were washed with brine (20 ml), dried w/Mg2SO4, filtered and concentrated. The crude product was flash chromatographed (50 mm; 0.5 L 2% methanol in CH2Cl2 to 4% methanol in CH2Cl2) to afford the desired product.

Workup

  1. extractionthe separated aqueous phase was extracted with ethyl acetate (4×20 ml)
  2. washthe combined organic layers were washed with brine (20 ml)
  3. dry with materialdried w/Mg2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed (50 mm; 0.5 L 2% methanol in CH2Cl2 to 4% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-a1145566b014435090808a4f285cd19f
Source dataset
uspto-grants-2013_04
Patent number
US08426408B2

Reaction notes

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