Formaldehyde → HCID 86729393, compound

HRID 521226Notes

Reaction equation

HRID 521226 reaction equation
F[C:2](F)(F)C([O-])=O.[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].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O.C([O-])(O)=O.[Na+]>ClCCCl>[C:21]([CH2:20][C:16]1([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)[CH2:17][N:18]([CH3:2])[CH2:19]1)#[N:22]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86729391HCID 86729391, compound

Product 1

HCID 86729393HCID 86729393, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

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 DCE (2.0 mL) was added sodium triacetoxyborohydride (79 mg, 0.37 mmol), followed by formaldehyde (0.050 mL, 0.67 mmol, 37 wt % in water). The resulting mixture was allowed to stir for 1 hour before saturated aqueous NaHCO3 solution was added and the resulting 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 0-100%, EtOAc/hexanes) to afford the title compound, Example #20.

Workup

  1. additionwas added
  2. extractionthe resulting mixture was extracted with EtOAc (3×)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by MPLC on silica gel (
  7. washa gradient elution of 0-100%, EtOAc/hexanes)

Sources & evidence

ORD record
ord-073395f4bc5c41d1b7254b17b45aa610
Source dataset
uspto-grants-2016_05
Patent number
US09328099B2

Reaction notes

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