Nitrogen → HCID 67212646, compound

HRID 554675Notes

Reaction equation

HRID 554675 reaction equation
[CH2:1]([O:3][C:4](=[O:38])[CH2:5][C:6]1[CH:7]=[N:8][C:9]([O:36][CH3:37])=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=2[CH2:22][N:23](C(OCC2C=CC=CC=2)=O)[CH2:24][CH3:25])[CH:11]=1)[CH3:2].C([O-])=O.[NH4+].N#N>[Pd].CO>[CH2:1]([O:3][C:4](=[O:38])[CH2:5][C:6]1[CH:7]=[N:8][C:9]([O:36][CH3:37])=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:21])[F:20])=[CH:14][C:13]=2[CH2:22][NH:23][CH2:24][CH3:25])[CH:11]=1)[CH3:2]

Participants

6

Reactant 3

HCID 947NitrogenHCID 2723923Ammonium formateHCID 67212435HCID 67212435, compound

Product 1

HCID 67212646HCID 67212646, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(5-{2-[(N-Benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-6-methoxy-pyridin-3-yl)-acetic acid ethyl ester (0.700 g, 1.3 mmol), ammonium formate (0.164 g, 2.6 mmol), and palladium on carbon (10%; 0.138 g) were combined in an evacuated flask that was backfilled with N2. MeOH (10 mL) was added, and the resulting suspension was stirred at room temperature for 3 hours. A balloon of H2 was added, and the reaction was stirred under an atmosphere of H2 overnight at room temperature. The mixture was filtered through Celite, and the filtrate was concentrated. The residue was dissolved in EtOAc and washed with H2O and brine, and then dried over Na2SO4, filtered, and concentrated. The crude material was purified by silica gel chromatography (0-5% MeOH in CH2Cl2) to give [5-(2-ethylaminomethyl-4-trifluoromethyl-phenyl)-6-methoxy-pyridin-3-yl]-acetic acid ethyl ester, which was subsequently reacted with acetyl chloride as described in Example 5, Step 4 to provide (5-{2-[(N-acetyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-6-methoxy-pyridin-3-yl)-acetic acid ethyl ester. The ester was hydrolyzed to the acid as described in Example 3, Step 7.

Workup

  1. additionA balloon of H2 was added
  2. stirringthe reaction was stirred under an atmosphere of H2 overnight at room temperature
  3. filtrationThe mixture was filtered through Celite
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was dissolved in EtOAc
  6. washwashed with H2O and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude material was purified by silica gel chromatography (0-5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-b499c699ddaf4a15b6c485cf902a7cfa
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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