O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → HCID 66920563, compound

HRID 1364543Notes

Reaction equation

HRID 1364543 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: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]([NH2:38])[CH:40]=2)=[O:15])[CH:3]=1

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 46288313-AminobenzylamineHCID 118464604-Amino-5-cyano-6-ethoxypicolinic acid

Product 1

HCID 66920563HCID 66920563, compound

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-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 1.27-1.39 (m, 3H) 4.18-4.75 (m, 4H) 6.31-7.50 (m, 5H). MS (ESI) positive ion 312 (M+H)+

Workup

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

Sources & evidence

ORD record
ord-c04a2b674b074f38b132c77ffc3af2f4
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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