Ammonium formate → HCID 131722691, compound

HRID 278207Notes

Reaction equation

HRID 278207 reaction equation
C([O-])=O.[NH4+].[OH:5][C:6]([C:8]([F:11])([F:10])[F:9])=[O:7].[OH:12][C:13]([C:15]([F:18])([F:17])[F:16])=[O:14].[C:19]1([CH2:25][CH2:26][C:27]2[CH:28]=[N:29][N:30]([CH2:45][CH3:46])[C:31]=2[CH:32]2[CH2:37][CH2:36][N:35](CC3C=CC=CC=3)[CH2:34][CH2:33]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CO.[OH-].[OH-].[Pd+2]>[OH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[O:5].[OH:14][C:13]([C:15]([F:18])([F:17])[F:16])=[O:12].[C:19]1([CH2:25][CH2:26][C:27]2[CH:28]=[N:29][N:30]([CH2:45][CH3:46])[C:31]=2[CH:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 131722692HCID 131722692, compound

Product 1

HCID 131722691HCID 131722691, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ammonium formate (119 mg), 20% Pd(OH)2/C (5 mg) and 4-(4-(2-phenylethyl)-1-ethyl-(1H-pyrazol-5-yl))-1-benzylpiperidine di-TFA salt from Step F in methanol (2 mL) was heated at 60° C. for 1.5 h. The solvent was removed under reduced pressure and the residue was purified by preparative reverse-phase HPLC using a 9.4×250 mm Semi-preparative Zorbax SB-C18 column with 20-35% acetonitrile gradient in water having 0.5% (v/v) TFA over 15 min at 6.25 mL per min to give the title compound as the di-TFA salt (25 mg) as a gel.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by preparative reverse-phase
  3. customover 15 min

Sources & evidence

ORD record
ord-1abc7ff8d97a48bcbe02b0d6d9caaaee
Source dataset
uspto-grants-2002_03
Patent number
US06358979B1

Reaction notes

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