Hydrochloric Acid → 7-(benzylamino)-N-(4-pyridinylmethyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamide

HRID 1821846Notes

Reaction equation

HRID 1821846 reaction equation
[H][H].[CH2:3]([N:10](CC1C=CC=CC=1)[C:11]1[N:12]=[CH:13][CH:14]=[C:15]2[CH:19]=[C:18]([C:20]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)=[O:21])[NH:17][C:16]=12)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>[Pd].C(O)C>[CH2:3]([NH:10][C:11]1[N:12]=[CH:13][CH:14]=[C:15]2[CH:19]=[C:18]([C:20]([NH:22][CH2:23][C:24]3[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=3)=[O:21])[NH:17][C:16]=12)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 578934767-(dibenzylamino)-N-(4-pyridinylmethyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 578935117-(benzylamino)-N-(4-pyridinylmethyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamideYield 24.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Hydrogen (1 atm, balloon) was applied to a slurry of 7-(dibenzylamino)-N-(4-pyridinylmethyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamide (Example 41) (69 mg, 0.15 mmol), 10% palladium on carbon (wet, 100 mg) and HCl (saturated solution in 2-propanol, 5 M, 0.5 mL) in ethanol (4.5 mL) at room temperature for 3 h. The slurry was filtered to remove the catalyst, and the filtrate was concentrated in vacuo. The residue was partitioned between ethyl acetate and aqueous sodium hydrogen carbonate. The two layers were separated. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 2:1 to 1:2 hexanes/ethyl acetate). Recrystallization from hexanes/ethyl acetate gave 7-(benzylamino)-N-(4-pyridinylmethyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamide (13.2 mg, 24%) as colorless crystals: Rf 0.42 (silica gel, 20:80 methanol/ethyl acetate); mp 199-200° C. (recrystallized from hexanes/ethyl acetate); 1H NMR (300 MHz, CD3OD) δ4.63 (2H, s), 4.69 (2H, s), 6.91 (1H, d, J=6.0 Hz), 7.05 (1H, s), 7.22-7.43 (7H, m), 7.55 (1H, d, J=6.0 Hz), 8.48 (2H, d, J=6.0 Hz); ESI MS m/z 358 [C21H19N5O+H]+; HPLC (Method A) >99% (AUC), tR=13.2 min.

Workup

  1. filtrationThe slurry was filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was partitioned between ethyl acetate and aqueous sodium hydrogen carbonate
  5. customThe two layers were separated
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (silica gel, 2:1 to 1:2 hexanes/ethyl acetate)
  9. customRecrystallization from hexanes/ethyl acetate

Sources & evidence

ORD record
ord-b2fa1a35e594481cbe2fe43decaa76a0
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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