Triethylamine → N-(3-methoxyphenyl)-4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

HRID 216033Notes

Reaction equation

HRID 216033 reaction equation
[CH3:1][C:2]1([C:18]([OH:20])=O)[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][O:56][C:57]1[CH:58]=[C:59]([CH:61]=[CH:62][CH:63]=1)[NH2:60]>CN(C=O)C>[CH3:55][O:56][C:57]1[CH:58]=[C:59]([NH:60][C:18]([C:2]2([CH3:1])[CH2:7][CH2:6][N:5]([C:8]3[C:9]4[C:16]([CH3:17])=[CH:15][NH:14][C:10]=4[N:11]=[CH:12][N:13]=3)[CH2:4][CH2:3]2)=[O:20])[CH:61]=[CH:62][CH:63]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 108243-MethoxyanilineHCID 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 44482112N-(3-methoxyphenyl)-4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamideYield 328.5%

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 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 3-methoxyaniline (0.012 mL, 0.11 mmol). The reaction was stirred overnight, and then concentrated under vacuum. The residue was purified by prep HPLC to give the title compound (0.091 g, 33%).

Workup

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

Sources & evidence

ORD record
ord-7f0b842ea83948049a120dd6d9bdcaa1
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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