p-Toluidine → 4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-N-p-tolylpiperidine-4-carboxamide

HRID 216034Notes

Reaction equation

HRID 216034 reaction equation
[CH3:1][C:2]1([C:18](O)=[O:19])[CH2:7][CH2:6][N:5]([C:8]2[C:9]3[C:16]([CH3:17])=[CH:15][NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH2:4][CH2:3]1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[CH3:55][C:56]1[CH:62]=[CH:61][C:59]([NH2:60])=[CH:58][CH:57]=1>CN(C=O)C>[CH3:1][C:2]1([C:18]([NH:60][C:59]2[CH:61]=[CH:62][C:56]([CH3:55])=[CH:57][CH:58]=2)=[O:19])[CH2:3][CH2:4][N:5]([C:8]2[C:9]3[C:16]([CH3:17])=[CH:15][NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 7813p-ToluidineHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 670367814-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4yl)-piperidine-4-carboxylic acid

Product 1

HCID 579201954-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-N-p-tolylpiperidine-4-carboxamideYield 50.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4yl)-piperidine-4-carboxylic acid from example 6, step B, (0.020 g, 0.073 mmol) in DMF (1 mL) were added BOP reagent (0.065 g, 0.15 mmol), triethylamine (0.019 mL, 0.15 mmol), and 4-methylaniline (0.012 mL, 0.11 mmol). The reaction was stirred overnight and concentrated under vacuum. The residue was purified by prep HPLC to give the title compound (0.0133 g, 50%).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-c7913e08e31c40d6bc02d8fd6e0b6e99
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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