Pyridoxal 5'-phosphate monohydrate → N-(4-Bromophenyl)-2-(4-methyl-piperidin-1-yl)-5-amino-benzoic acid amide

HRID 1846101Notes

Reaction equation

HRID 1846101 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:26])[C:10]2[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:11]=2[N:19]2[CH2:24][CH2:23][CH:22]([CH3:25])[CH2:21][CH2:20]2)=[CH:4][CH:3]=1.CC1C(O)=C(C=O)C(COP(O)(O)=O)=CN=1.O>C1COCC1.[Ni]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:26])[C:10]2[CH:15]=[C:14]([NH2:16])[CH:13]=[CH:12][C:11]=2[N:19]2[CH2:20][CH2:21][CH:22]([CH3:25])[CH2:23][CH2:24]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 38882Pyridoxal 5'-phosphate monohydrateHCID 67116648N-(4-bromophenyl)-2-(4-methyl-piperidin-1-yl)-5-nitro-benzoic acid amide

Product 1

HCID 67116511N-(4-Bromophenyl)-2-(4-methyl-piperidin-1-yl)-5-amino-benzoic acid amide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Prepared analogously to Example 4b from N-(4-bromophenyl)-2-(4-methyl-piperidin-1-yl)-5-nitro-benzoic acid amide and Ra-Ni in THF. Yield: (quantitative). MS [M+H]+=388 (Br-isotope pattern); Rt=1.36 min (Method MC-1).

Sources & evidence

ORD record
ord-21e6ea9ec1f24652bd1c712c171afbce
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

Loading…