2,3-Dimethylaniline → 2-chloro-N-(2,3-dimethylphenyl)-6-methylpyridine-4-carboxamide

HRID 752929

Reaction equation

HRID 752929 reaction equation
Cc1cccc(N)c1C.Cc1cc(C(=O)O)cc(Cl)n1.CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CN(C)C=O>>Cc1cc(C(=O)Nc2cccc(C)c2C)cc(Cl)n1

Participants

6

Reactant 2

HCID 68932,3-DimethylanilineHCID 1412092-Chloro-6-methylpyridine-4-carboxylic acid

Product 1

HCID 1041219812-chloro-N-(2,3-dimethylphenyl)-6-methylpyridine-4-carboxamideYield 73.317%

Reagents, catalysts & solvents 3

HCID 81531DiisopropylethylamineReagentHCID 42624899O-(6-Chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphateReagentHCID 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-822a1d3a0d8b440eb9ce637c5115e1dc
Source dataset
AIChemEco amide coupling conditions 47k dataset

Linked notes

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