Benzylamine → 4-amino-N-benzyl-5-cyano-6-ethoxypyridine-2-carboxamide

HRID 1364538Notes

Reaction equation

HRID 1364538 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.[CH2:38]([NH2:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>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:45][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[O:15])[CH:3]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 118464604-Amino-5-cyano-6-ethoxypicolinic acid

Product 1

HCID 118464614-amino-N-benzyl-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 benzylamine (11 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-D6D2O) δ ppm 1.31 (t, 3H) 4.43-4.54 (m, 4H) 7.06-7.11 (m, 1H) 7.21-7.36 (m, 5H) 9.07-9.14 (m, 1H).

Workup

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

Sources & evidence

ORD record
ord-a37f099de09048609da3fff2fbe23a97
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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