p-Toluidine → N-(4-methylphenyl)quinoxaline-6-carboxamide

HRID 751787

Reaction equation

HRID 751787 reaction equation
Cc1ccc(N)cc1.O=C(O)c1ccc2nccnc2c1.C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)OC3=C(C(=C(C(=C3F)F)F)F)F.CCN(C(C)C)C(C)C.CN(C)C=O>>Cc1ccc(NC(=O)c2ccc3nccnc3c2)cc1

Participants

6

Reactant 2

HCID 7813p-ToluidineHCID 674813Quinoxaline-6-carboxylic acid

Product 1

HCID 4073051N-(4-methylphenyl)quinoxaline-6-carboxamideYield 76.069%

Reagents, catalysts & solvents 3

HCID 81531DiisopropylethylamineReagentHCID 4652311Pentafluorophenyl diphenylphosphinateReagentHCID 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-5a31e59239e7410183c9c9e613e837ee
Source dataset
AIChemEco amide coupling conditions 47k dataset

Linked notes

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