Ammonium formate → HCID 59127171, compound

HRID 1990194Notes

Reaction equation

HRID 1990194 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:29])[C:9]2[CH:14]=[C:13]([O:15][C@H:16]3[CH2:20][CH2:19][O:18][CH2:17]3)[CH:12]=[C:11]([O:21]CC3C=CC=CC=3)[CH:10]=2)=[N:3]1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[OH:21][C:11]1[CH:10]=[C:9]([CH:14]=[C:13]([O:15][C@H:16]2[CH2:20][CH2:19][O:18][CH2:17]2)[CH:12]=1)[C:8]([NH:7][C:4]1[CH:5]=[CH:6][N:2]([CH3:1])[N:3]=1)=[O:29]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 53629650N-(1-Methyl-1H-pyrazol-3-yl)-3-[(phenylmethyl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzamide

Product 1

HCID 59127171HCID 59127171, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

N-(1-Methyl-1H-pyrazol-3-yl)-3-[(phenylmethyl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzamide (453 mg, 1.15 mmol) was dissolved in ethanol (5 mL) and ammonium formate (182 mg, 2.88 mmol) was added in one portion. The reaction was blanketed with argon and 10% palladium on activated carbon (30 mg) was added. This mixture was heated to 140° C. for 10 minutes in a Smith Creator microwave. The catalyst was filtered off and the volatiles removed in vacuo to give the title product as a white solid (339 mg).

Workup

  1. additionwas added
  2. filtrationThe catalyst was filtered off
  3. customthe volatiles removed in vacuo

Sources & evidence

ORD record
ord-a85013d59d2a498baa4304f2da9a3fd8
Source dataset
uspto-grants-2010_01
Patent number
US07642259B2

Reaction notes

Loading…