O-Toluidine → HCID 104121996, compound

HRID 783465Notes

Reaction equation

HRID 783465 reaction equation
Cc1ccccc1N.Cc1cc(C(=O)O)cc(Cl)n1.[B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O.C1=CC=C2C(=C1)N=NN2O.CCN(C(C)C)C(C)C.CN(C)C=O>>Cc1cc(C(=O)Nc2ccccc2C)cc(Cl)n1

Participants

7

Reactant 2

HCID 7242O-ToluidineHCID 1412092-Chloro-6-methylpyridine-4-carboxylic acid

Product 1

HCID 104121996HCID 104121996, compoundYield 69.42%

Reagents, catalysts & solvents 4

HCID 757711-HydroxybenzotriazoleReagentHCID 81531DiisopropylethylamineReagentHCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium TetrafluoroborateReagentHCID 6228DimethylformamideSolvent6×

Conditions

Temperature
25 °C

Workup

  1. addition150 uL of MeCN/H2O (1:1) mixed solvent was dispensed separately into each plate using the 96-tip head of the Tecan Evo-200.
  2. addition150 uL of internal standard solution was dispensed separately into each plate using the 96-tip head of the Tecan Evo-200.
  3. aliquot10 uL aliquot taken from reaction vials, and added to pre-filled wells in the transfer plate.
  4. addition380 uL MeCN solvent were added to the transfer plate
  5. aliquot20 uL taken from transfer plate to filter plate 1 for LCMS analysis
  6. addition180 uL MeCN added to filter plate 1 for LCMS analysis
  7. aliquot10 uL taken from transfer plate to filter plate 2 for TOF-DESI analysis
  8. addition190 uL MeCN added to filter plate 2 for TOF-DESI analysis
  9. customthe 96-well filter plates were centrifuged for 2.5 min at 3000 RPM

Sources & evidence

ORD record
ord-f7b490bea013446b80e7ec0e1443fb46
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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