Ammonium formate → HCID 58168380, compound

HRID 1029131Notes

Reaction equation

HRID 1029131 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]#[C:10][C:11]2[CH:20]=[CH:19][N:18]=[C:17]3[C:12]=2[C:13]2[CH:25]=[CH:24][CH:23]=[CH:22][C:14]=2[C:15](=[O:21])[NH:16]3)[CH:6]=[CH:7][CH:8]=1.C([O-])=O.[NH4+]>O1CCOCC1.[Pd].[C]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][N:18]=[C:17]3[C:12]=2[C:13]2[CH:25]=[CH:24][CH:23]=[CH:22][C:14]=2[C:15](=[O:21])[NH:16]3)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 58168328HCID 58168328, compound

Product 1

HCID 58168380HCID 58168380, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

Compound 160 (45 mg, 0.14 mmol), ammonium formate (100 mg, 1.60 mmol), and Pd/carbon (100 mg, 10% by weight, wet) were suspended in dioxane (2 mL), and stirred for 4 h at 70° C. The reaction mixture was filtered, and purified via Biotage eluting with a gradient of 25 to 75 EtOAc in hexanes to provide 162 (14 mg, 31% yield) as a white solid. LC-MS (M+H=331, obsd.=331).

Workup

  1. filtrationThe reaction mixture was filtered
  2. custompurified via Biotage
  3. washeluting with a gradient of 25 to 75 EtOAc in hexanes

Sources & evidence

ORD record
ord-026e1fcfbc284fc3af8a68993436ea89
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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