Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → 1-methyl-N-(4-{[4-(methylamino)-3-nitrophenyl]oxy}pyridin-2-yl)piperidine-4-carboxamide

HRID 30780

Reaction equation

HRID 30780 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=O)[CH2:4][CH2:3]1.F[P-](F)(F)(F)(F)F.[N:18]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:22]2C=CC=CC=2N=N1.[NH2:38][C:39]1[CH:44]=[C:43]([O:45][C:46]2[CH:51]=[CH:50][C:49](CN)=[C:48]([N+:54]([O-:56])=[O:55])[CH:47]=2)[CH:42]=[CH:41][N:40]=1>CN(C)C=O>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([C:8]([NH:38][C:39]2[CH:44]=[C:43]([O:45][C:46]3[CH:51]=[CH:50][C:49]([NH:18][CH3:22])=[C:48]([N+:54]([O-:56])=[O:55])[CH:47]=3)[CH:42]=[CH:41][N:40]=2)=[O:10])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27369391-Methylpiperidine-4-carboxylic acidHCID 69006232[4-(2-Amino(4-pyridyloxy))-2-nitrophenyl]methylamine

Product 1

HCID 690032661-methyl-N-(4-{[4-(methylamino)-3-nitrophenyl]oxy}pyridin-2-yl)piperidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-methylpiperidine-4-carboxylic acid (1 eq) in N,N-dimethyl formamide and N,N-disopropylethylamine (4 eq) was added BOP (2 eq) and the mixture was stirred at ambient temperature until homogeneous. To it was added [4-(2-amino(4-pyridyloxy))-2-nitrophenyl]methylamine (1 eq) and the resulting mixture was stirred at 60° C. for 16 h. The reaction mixture was then concentrated and partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate and the resulting 1-methyl-N-(4-{[4-(methylamino)-3-nitrophenyl]oxy}pyridin-2-yl)piperidine-4-carboxamide was purified by silica gel chromatography. MS: MH+=386.2.

Workup

  1. stirringthe resulting mixture was stirred at 60° C. for 16 h
  2. concentrationThe reaction mixture was then concentrated
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe resulting 1-methyl-N-(4-{[4-(methylamino)-3-nitrophenyl]oxy}pyridin-2-yl)piperidine-4-carboxamide was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a174a43a92334bcdb6c395c164189f26
Source dataset
uspto-grants-2008_09
Patent number
US07423150B2

Linked notes

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