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

HRID 1364539Notes

Reaction equation

HRID 1364539 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: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[CH3:38])=[O:15])[CH:3]=1

Participants

5

Reactant 3

HCID 69932-MethylbenzylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 118464604-Amino-5-cyano-6-ethoxypicolinic acid

Product 1

HCID 669206414-amino-5-cyano-6-ethoxy-N-(2-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 2-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 1.31 (t, 3H) 2.28-2.34 (m, 3H) 4.38-4.55 (m, 4H) 7.05-7.10 (m, 1H) 7.11-7.21 (m, 4H) 8.92-8.99 (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-b798384fcc9444e6ab912c5b0067d38b
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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