Ammonium formate → HCID 178510258, compound

HRID 1623258Notes

Reaction equation

HRID 1623258 reaction equation
C([O:8][C:9]1[N:14]=[C:13]([NH:15][CH2:16][CH:17]2[CH2:22][CH:21]([C:23]#[N:24])[CH2:20][CH2:19][O:18]2)[C:12]([F:25])=[CH:11][CH:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[F:25][C:12]1[C:13]([NH:15][CH2:16][CH:17]2[CH2:22][CH:21]([C:23]#[N:24])[CH2:20][CH2:19][O:18]2)=[N:14][C:9]([OH:8])=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86689270HCID 86689270, compound

Product 1

HCID 178510258HCID 178510258, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-(((6-(benzyloxy)-3-fluoropyridin-2-ylamino)methyl)tetrahydro-2H-pyran-4-carbonitrile (200 mg, 0.586 mmol), AMMONIUM FORMATE (111.3 mg, 1.758 mmol) and Pd—C (10%, wet, 25 mg) in methanol (4 ml) was stirred at 70° C. for 45 min and cooled. The mixture was then filtered to remove Pd—C and inorganics, the filterate was then concentrated and dried further via high vacuum to afford 141 mg (96% yield) of the crude product as a light pink solid. LCMS (m/z): 252.1 [M+H]+; retention time=0.540 min.

Workup

  1. temperaturecooled
  2. filtrationThe mixture was then filtered
  3. customto remove Pd—C and inorganics
  4. concentrationthe filterate was then concentrated
  5. customdried further via high vacuum

Sources & evidence

ORD record
ord-203900ba97e64914ab7ad66e18e2ddab
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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