Pyridine → HCID 86729413, compound

HRID 521238Notes

Reaction equation

HRID 521238 reaction equation
F[C:2](F)(F)[C:3]([O-])=[O:4].[C:8]([C:11]1[C:12]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:13][N:14]([C:16]2([CH2:20][C:21]#[N:22])[CH2:19][NH2+:18][CH2:17]2)[CH:15]=1)(=[O:10])[NH2:9].N1C=CC=CC=1.C(OC(=O)C)(=O)C>C(Cl)Cl>[C:3]([N:18]1[CH2:17][C:16]([N:14]2[CH:15]=[C:11]([C:8]([NH2:9])=[O:10])[C:12]([NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:13]2)([CH2:20][C:21]#[N:22])[CH2:19]1)(=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 86729391HCID 86729391, compound

Product 1

HCID 86729413HCID 86729413, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-[4-carbamoyl-3-(phenylamino)-1H-pyrazol-1-yl]-3-(cyanomethyl)azetidinium trifluoroacetate (Intermediate #38-2) (50 mg, 0.17 mmol) in DCM (2 mL) was added pyridine (0.050 mL, 0.62 mmol), followed by acetic anhydride (0.030 mL, 0.32 mmol). The reaction mixture was allowed to stir for 30 minutes before the solvent was removed in vacuo. Saturated aqueous NaHCO3 solution was added and the mixture was extracted with EtOAc (3×). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified by MPLC on silica gel (using a gradient elution of 50-100% EtOAc/hexanes followed by 10% MeOH/EtOAc) to afford the title compound, Example #32.

Workup

  1. customwas removed in vacuo
  2. additionSaturated aqueous NaHCO3 solution was added
  3. extractionthe mixture was extracted with EtOAc (3×)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by MPLC on silica gel (
  8. washa gradient elution of 50-100% EtOAc/hexanes

Sources & evidence

ORD record
ord-f2817e4af0814d4ba255b7536f012ead
Source dataset
uspto-grants-2016_05
Patent number
US09328099B2

Reaction notes

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