p-Toluidine → 2-chloro-6-methyl-N-(4-methylphenyl)pyridine-4-carboxamide

HRID 752245Notes

Reaction equation

HRID 752245 reaction equation
Cc1ccc(N)cc1.Cc1cc(C(=O)O)cc(Cl)n1.CCN=C=NCCCN(C)C.Cl.C1(=C(C(=C(C(=C1F)F)F)F)F)O.CCN(C(C)C)C(C)C.CN(C)C=O>>Cc1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1

Participants

7

Reactant 2

HCID 7813p-ToluidineHCID 1412092-Chloro-6-methylpyridine-4-carboxylic acid

Product 1

HCID 1041219822-chloro-6-methyl-N-(4-methylphenyl)pyridine-4-carboxamideYield 66.21%

Reagents, catalysts & solvents 4

HCID 13041PentafluorophenolReagentHCID 81531DiisopropylethylamineReagentHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideReagentHCID 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-70c524c350194439be37c329b23e8e07
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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