Ammonium formate → HCID 71657497, compound

HRID 1521899Notes

Reaction equation

HRID 1521899 reaction equation
[CH2:1]([O:3][C:4](=[O:34])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:15]2=[N:16][C:17]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)[N:19]=[C:14]2[CH:13]=[CH:12]1)[CH3:2].C([O-])=O.[NH4+]>CCO.[Pd]>[C:23]1([CH3:26])[CH:22]=[CH:21][C:20]([C:18]2[N:19]=[C:14]3[CH2:13][CH2:12][N:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:34])[C:15]3=[N:16][C:17]=2[C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 71657498HCID 71657498, compound2×

Product 1

HCID 71657497HCID 71657497, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

7-(2,3-Di-p-tolyl-pyrrolo[2,3-b]pyrazin-5-yl)-heptanoic acid ethyl ester (Intermediate B) (35 mg, 0.077 mmol) in dry EtOH (1 ml) under nitrogen at RT was treated with ammonium formate (24.22 mg, 0.384 mmol) followed by Pd on carbon (8.18 mg, 7.68 μmol). The resulting black suspension was heated at reflux for 16 hours, overnight. The reaction mixture was cooled to RT and then loaded onto a Celite® (filter material) column. The column was eluted with 1:1 MeOH/DCM and the filtrate concentrated under reduced pressure. The resultant residue was dissolved in DCM (50 ml), washed with water (×2) and the organic solvent removed under reduced pressure. Purification by chromatography on silica eluting with 0-30% EtOAc in iso-hexane afforded the titled compound;

Workup

  1. temperatureThe resulting black suspension was heated
  2. temperatureat reflux for 16 hours, overnight
  3. filtrationloaded onto a Celite® (filter material) column
  4. washThe column was eluted with 1:1 MeOH/DCM
  5. concentrationthe filtrate concentrated under reduced pressure
  6. dissolutionThe resultant residue was dissolved in DCM (50 ml)
  7. washwashed with water (×2)
  8. customthe organic solvent removed under reduced pressure
  9. customPurification by chromatography on silica eluting with 0-30% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-4fc034d254eb4c6597c242b9e0330210
Source dataset
uspto-grants-2015_07
Patent number
US09073932B2

Reaction notes

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