HCID 21073256, compound → HCID 21073470, compound

HRID 1373571Notes

Reaction equation

HRID 1373571 reaction equation
C([O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[N:12][C:13]([O:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][N:25]([C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[C:29]=4[Cl:35])[CH2:24][CH2:23]3)=[CH:14][CH:15]=2)[N:10]=1)C1C=CC=CC=1>CO.[Pd]>[Cl:35][C:29]1[C:30]([Cl:34])=[CH:31][CH:32]=[CH:33][C:28]=1[N:25]1[CH2:24][CH2:23][N:22]([CH2:21][CH2:20][O:19][C:13]2[N:12]=[C:11]3[C:16]([CH:17]=[CH:18][C:9](=[O:8])[NH:10]3)=[CH:15][CH:14]=2)[CH2:27][CH2:26]1

Participants

4

Reactant 1

HCID 21073256HCID 21073256, compound

Product 1

HCID 21073470HCID 21073470, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Benzyloxy-7-{2-[4-(2,3-dichloro-phenyl)-piperazin-1-yl]-ethoxy}-[1,8]naphthyridine (1.30 g, 2.55 mmol) was hydrogenated using 5% Pd/C (0.4 g) in MeOH (100 mL) for 40 min. The reaction was filtered and concentrated. Purification by liquid chromatography (2–3% MeOH/EtOAc with 1% NH4OH) gave the title compound as a white foam (600 mg, 1.43 mmol, 56%). The HCl salt was prepared using 1 N HCl in Et2O to give a white solid. MS: APCI: M+1: 419.1 (Exact Mass: 418.10).

Workup

  1. customfor 40 min
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. customPurification by liquid chromatography (2–3% MeOH/EtOAc with 1% NH4OH)

Sources & evidence

ORD record
ord-f27d2937a3fd45299b3a6558dc19df79
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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