Ammonium formate → HCID 86271579, compound

HRID 2177622Notes

Reaction equation

HRID 2177622 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]([N:14]1[CH:19]=[CH:18][C:17]2[N:20]([C:23]3[CH:24]=[N:25][CH:26]=[N:27][CH:28]=3)[N:21]=[N:22][C:16]=2[CH:15]1[CH3:29])=[O:13].C([O-])=O.[NH4+]>CO.[Pd].[C]>[Cl:1][C:2]1[C:7]([C:8]([F:9])([F:11])[F:10])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]([N:14]1[CH2:19][CH2:18][C:17]2[N:20]([C:23]3[CH:24]=[N:25][CH:26]=[N:27][CH:28]=3)[N:21]=[N:22][C:16]=2[CH:15]1[CH3:29])=[O:13]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 90408624HCID 90408624, compound

Product 1

HCID 86271579HCID 86271579, compoundYield 102.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A solution of (2-chloro-3-(trifluoromethyl)phenyl)(4-methyl-1-(pyrimidin-5-yl)-1H-[1,2,3]triazolo[4,5-c]pyridin-5(4H)-yl)methanone (237 mg, 0.56 mmol) in MeOH (12 ml) was treated with ammonium formate (147 mg, 2.3 mmol) and Pd/carbon (10 wt %, 20 mg) and the reaction was refluxed for 90 min. The reaction was filtered through celite and the filter cake washed with MeOH and concentrated to a crude solid which was re-suspended with CHCl3 and filtered to remove in-organic salts then purified on 40 g SiO2 with 0-60% EtOAc hexanes to provide 243 mg (22%) of desired product. MS (ESI) mass calcd. C18H14ClF3N6O, 422.09. m/z found, 423.1 [M+H]+. The enantiomers were separated by chiral SFC on (CHIRALPAK AD-H 5 μm 250×20 mm). Mobile phase (70% CO2, 30% EtOH).

Workup

  1. temperaturethe reaction was refluxed for 90 min
  2. filtrationThe reaction was filtered through celite
  3. washthe filter cake washed with MeOH
  4. concentrationconcentrated to a crude solid which
  5. filtrationfiltered
  6. customto remove in-organic salts
  7. customthen purified on 40 g SiO2 with 0-60% EtOAc hexanes

Sources & evidence

ORD record
ord-e2d4c9eccda44d05ad18ff61498ab952
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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