Sulfuric Acid → HCID 71073961, compound

HRID 882571Notes

Reaction equation

HRID 882571 reaction equation
[NH:1]1[C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]([C:9]([OH:11])=O)=[N:2]1.[CH2:12]([O:14][C:15](=[O:27])[CH2:16][C@H:17]([NH2:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:25])[CH3:13].CN(C(ON1N=N[C:38]2C=CC=N[C:37]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.OS(O)(=O)=O>CN(C=O)C.CCO.CCOC(C)=O>[CH2:37]([O:8][C:6]([C:5]1[NH:1][N:2]=[C:3]([C:9](=[O:11])[NH:26][C@H:17]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[CH2:16][C:15]([O:14][CH2:12][CH3:13])=[O:27])[CH:4]=1)=[O:7])[CH3:38]

Participants

9

Reactant 5

HCID 1118Sulfuric AcidHCID 76559Pyrazole-3,5-dicarboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71073521HCID 71073521, compound

Product 1

HCID 71073961HCID 71073961, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3,5-Pyrazoledicarboxylic acid (840 mg, 5.4 mmol, 1.0 eq.), (R)-3-amino-4-(2-chloro-phenyl)-butyric acid ethyl ester (1.3 g, 5.4 mmol, 1.0 eq.), and HATU (2.0 g, 5.4 mmol, 1.0 eq.) were combined in DMF (5 mL) and mixed with sonication. DIPEA (1.9 mL, 10.8 mmol, 2.0 eq.) was added and the mixture was stirred for 1 hour at room temperature, then vacuumed to dryness. The crude product was dissolved in EtOH (25 mL), and concentrated H2SO4 (100 μL) was added. The mixture was stirred at 80° C. for 3 hours, then vacuumed to near dryness. EtOAc (200 mL) was added and the product was washed with NaHCO3 (100 mL) and then saturated aqueous NaCl (100 mL). The organic layer was retained and dried over anhydrous MgSO4 for 10 minutes prior to filtration and evacuation to dryness to yield 5-[(R)-1-(2-chloro-benzyl)-2-ethoxycarbonyl-ethylcarbamoyl]-2H-pyrazole-3-carboxylic acid ethyl ester, which was used without further purification (1.1 g).

Workup

  1. additionmixed with sonication
  2. stirringThe mixture was stirred at 80° C. for 3 hours
  3. washthe product was washed with NaHCO3 (100 mL)
  4. dry with materialdried over anhydrous MgSO4 for 10 minutes
  5. filtrationto filtration and evacuation to dryness

Sources & evidence

ORD record
ord-bf706910347943388273bcecc6a55fe1
Source dataset
uspto-grants-2015_03
Patent number
US08993752B2

Reaction notes

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