Isonicotinic Acid → HCID 9949292, compound

HRID 989007Notes

Reaction equation

HRID 989007 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([OH:9])=O)=[CH:3][CH:2]=1.CN1CCOCC1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH3:44][O:45][C:46]1[CH:47]=[C:48]([N:54]2[CH2:59][CH2:58][NH:57][CH2:56][CH2:55]2)[CH:49]=[C:50]([O:52][CH3:53])[CH:51]=1>CN(C=O)C>[CH3:44][O:45][C:46]1[CH:47]=[C:48]([N:54]2[CH2:55][CH2:56][N:57]([C:7]([C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)=[O:9])[CH2:58][CH2:59]2)[CH:49]=[C:50]([O:52][CH3:53])[CH:51]=1

Participants

6

Reactant 4

HCID 5922Isonicotinic AcidHCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27362051-(3,5-Dimethoxyphenyl)piperazine

Product 1

HCID 9949292HCID 9949292, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5 g (45.8 mmol) of pyridine-4-carboxylic acid were suspended with stirring in 150 ml of DMF. With further stirring, 6.93 g (68.5 mmol) of N-methylmorpholine and then a solution of 35.6 g (68.5 mmol) of Py-BOP (1-benzotriazolyltripyrrolidinophosphonium hexafluorophosphate) and 10.18 g (45.8 mmol) of 1-(3,5-dimethoxyphenyl)piperazine in 60 ml of DMF were added to this mixture. The mixture was stirred at room temperature for 24 hours, the DMF was distilled off under reduced pressure and the residue was purified on a silica gel column (Kieselgel 60, from Merck AG, Darmstadt) using the mobile phase dichloromethane/methanol/25 percent ammonia (90:10:1 v/v/v).

Workup

  1. distillationthe DMF was distilled off under reduced pressure
  2. customthe residue was purified on a silica gel column (Kieselgel 60, from Merck AG, Darmstadt)

Sources & evidence

ORD record
ord-8bca516cd3e944f5ad98bfc2f2b45bad
Source dataset
uspto-grants-2003_10
Patent number
US06638935B2

Reaction notes

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