3-Methylbenzylamine → 4-amino-5-cyano-6-ethoxy-N-(3-methylbenzyl)pyridine-2-carboxamide

HRID 1364540Notes

Reaction equation

HRID 1364540 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.[CH3:38][C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][CH:46]=1)[CH2:42][NH2:43]>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:43][CH2:42][C:41]2[CH:44]=[CH:45][CH:46]=[C:39]([CH3:38])[CH:40]=2)=[O:15])[CH:3]=1

Participants

5

Reactant 3

HCID 660153-MethylbenzylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 118464604-Amino-5-cyano-6-ethoxypicolinic acid

Product 1

HCID 669207654-amino-5-cyano-6-ethoxy-N-(3-methylbenzyl)pyridine-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 3-methylbenzylamine (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 1.28-1.35 (m, 3H) 2.23-2.31 (m, 3H) 4.40-4.54 (m, 4H) 7.03-7.12 (m, 3H) 7.17-7.24 (m, 1H) 9.02-9.12 (m, 1H). MS (ESI) positive ion 311 (M+H)+; negative ion 309 (M−H)−.

Workup

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

Sources & evidence

ORD record
ord-88252d7e1dad4d6d9ecf4c8d7af25a18
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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