Ammonium formate → HCID 16747618, compound

HRID 1094473Notes

Reaction equation

HRID 1094473 reaction equation
[C:1]([NH:5][C:6](=[O:45])[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[N:9][C:8]=1[CH2:17][C@H:18]([OH:44])[C@H:19]([N:29](CC1C=CC=CC=1)CC1C=CC=CC=1)[CH2:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[F:28])([CH3:4])([CH3:3])[CH3:2].[NH4+].C([O-])=O>CO.O.[Pd]>[NH2:29][C@H:19]([CH2:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[F:28])[C@@H:18]([OH:44])[CH2:17][C:8]1[N:9]=[C:10]([C:13]([F:16])([F:14])[F:15])[CH:11]=[CH:12][C:7]=1[C:6]([NH:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:45]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 66639475HCID 66639475, compound

Product 1

HCID 16747618HCID 16747618, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To 10% Pd/C (0.94 g, 0.44 mmoles) in MeOH (40 mL) is added N-tert-Butyl-2-[(2S,3R)-3-dibenzylamino-4-(2,5-difluoro-phenyl)-2-hydroxy-butyl]-6-trifluoromethyl-nicotinamide (5.89 g, 9.42 mmoles) rinsed in with 19 mL of MeOH. To the reaction is added a solution of Formic Acid, Ammonium Salt (2.35 g, 37.4 mmol) in water 6.0 mL and heated to 40° C. for 20 minutes. The reaction is allowed to cool, the catalyst filtered, washed with MeOH and the organics concentrated under reduced pressure. The concentrate is taken up in MTBE and water to which is added NH4OH (pH˜10) and the aqueous layer extracted with MTBE. The organic phase is dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide the title compound.

Workup

  1. washrinsed in with 19 mL of MeOH
  2. temperatureto cool
  3. filtrationthe catalyst filtered
  4. washwashed with MeOH
  5. concentrationthe organics concentrated under reduced pressure
  6. additionwater to which is added NH4OH (pH˜10)
  7. extractionthe aqueous layer extracted with MTBE
  8. dry with materialThe organic phase is dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6618c5bf241845f89c72ca11261424a3
Source dataset
uspto-grants-2012_03
Patent number
US08133907B2

Reaction notes

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