Sodium Chloride → HCID 86593418, compound

HRID 1247846Notes

Reaction equation

HRID 1247846 reaction equation
S(O)(O)(=O)=O.[F:6][CH2:7][CH2:8][N:9]1[C:13]([NH2:14])=[C:12]([NH2:15])[CH:11]=[N:10]1.O=C1CCC(=O)N1[O:23][C:24](=O)[CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31].C(=O)([O-])O.[Na+].[Cl-].[Na+]>O1CCCC1>[NH2:14][C:13]1[N:9]([CH2:8][CH2:7][F:6])[N:10]=[CH:11][C:12]=1[NH:15][C:24](=[O:23])[CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 10684599Boc-Beta-Ala-OSuHCID 69462687HCID 69462687, compound

Product 1

HCID 86593418HCID 86593418, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1-(2-fluoroethyl)-1H-pyrazole-4,5-diamine sulfate (3 g) in tetrahydrofuran (30 ml) were added tert-butyl {3-[(2,5-dioxo-1-pyrrolidinyl)oxy]-3-oxopropyl}carbamate (3.9 g) and N,N-diisoporpylethylamine (3.5 g) under ice-cooling. The reaction mixture was stirred at room temperature for 2 hours. An aqueous sodium hydrogen carbonate solution and sodium chloride were added, and the mixture was extracted with ethyl acetate-tetrahydrofuran (three times). The organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate→ethyl acetate:ethanol=8:1) to give tert-butyl (3-{[5-amino-1-(2-fluoroethyl)-1H-pyrazol-4-yl]amino}-3-oxopropyl)carbamate (2.3 g).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate-tetrahydrofuran (three times)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate→ethyl acetate:ethanol=8:1)

Sources & evidence

ORD record
ord-096a1cd3f0504a95be7ba41c1050b414
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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