HCID 67198903, compound → HCID 67200218, compound

HRID 547563Notes

Reaction equation

HRID 547563 reaction equation
[ClH:1].[CH3:2][N:3]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)[C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][CH:6]=1>CO.[Pd]>[ClH:1].[NH2:11][C:8]1[CH:9]=[CH:10][C:5]([C:4]([N:3]([CH3:2])[C:15]2[CH:16]=[CH:17][C:18]([NH:21][C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)=[CH:19][CH:20]=2)=[O:14])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 67198903HCID 67198903, compound

Product 1

HCID 67200218HCID 67200218, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of amide 3 (3.46 g, 8.99 mmol) in MeOH (˜40 mL) was added a spatula tipful of 10% Pd/C, and the resulting suspension hydrogenated at 40 psi for 16 h. After this time, the reaction mixture was filtered through a pad of Celite, and solvent removed under reduced pressure. The residue was reprecipated from MeOH-EtOAc to give amine 4 as an amorphous cream solid (0.25 g, 15% from 1); mp 235-238° C. (powder -tar), 245-249° C. (gas evolved); 1H NMR: 13.85 (v br s, 1H, pyridine-N+—H), 10.75 (s, 1H, ArNHAr), 8.28 (d, J=7.23 Hz, 2H, ArH), 7.25 (s, 4H, ArH), 7.16 (d, J=8.44 Hz, 2H, ArH), 7.07 (d, J=7.03 Hz, 2H, ArH), 6.73 (d, J=7.79 Hz, 2H, ArH), 3.36 (s, ArC(O)N(CH3)Ar) [ArN+H3 not visible]; HRMS (EI) calc. for C19H18N4O m/z 318.1481, found 318.1481.

Workup

  1. filtrationAfter this time, the reaction mixture was filtered through a pad of Celite, and solvent
  2. customremoved under reduced pressure

Sources & evidence

ORD record
ord-16b2a9cf85434c92b2a0e6a288eafec7
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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