2-(Aminomethyl)aniline → 4-amino-N-(2-aminobenzyl)-5-cyano-6-ethoxypyridine-2-carboxamide

HRID 1364542Notes

Reaction equation

HRID 1364542 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([OH:15])=O)[CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH2:38][C:39]1[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=1[CH2:41][NH2:42]>CC(N(C)C)=O>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([NH:42][CH2:41][C:40]2[CH:43]=[CH:44][CH:45]=[CH:46][C:39]=2[NH2:38])=[O:15])[CH:3]=1

Participants

5

Reactant 3

HCID 1780962-(Aminomethyl)anilineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 118464604-amino-5-cyano-6-ethoxypicolinic acid

Product 1

HCID 669206764-amino-N-(2-aminobenzyl)-5-cyano-6-ethoxypyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent4×

Procedure

In a 20 mL scintillation vial, 4-amino-5-cyano-6-ethoxy-pyridine-2-carboxylic acid (19 mg, 0.09 mmol) was dissolved in DMA (0.7 mL). Then TBTU (30 mg, 0.09 mmol) dissolved in DMA (0.7 mL) was added, followed by the addition of 2-aminobenzylamine (12 mg, 0.11 mmol, 1.2 eq.) in DMA (0.6 mL). Then TEA (9.37 mg, 0.09 mmol) dissolved in DMA (0.7 mL) was added. The reaction mixture was shaken at room temperature for 24 hours. The crude mixture was purified using reverse phase HPLC (TFA). 1H NMR (500 MHz, DMSO-D6/D2O) δ ppm 1.27 (t, 3H) 4.21-4.37 (m, 2H) 4.45 (q, 2H) 6.33-7.25 (m, 5H). MS (ESI) negative ion 310 (M−H)−.

Workup

  1. additionwas added
  2. additionwas added
  3. customThe crude mixture was purified

Sources & evidence

ORD record
ord-a83518342419445bb423556d9dfc5022
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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