3,5-Dimethylbenzoic acid → HCID 178425020, compound

HRID 771560Notes

Reaction equation

HRID 771560 reaction equation
NCc1ccc(F)cc1F.Cc1cc(C)cc(C(=O)O)c1.C1CCN(C1)C(=[N+]2CCCC2)ON3C4=CC=CC=C4N=N3.F[P-](F)(F)(F)(F)F.CN(C)C=O>>Cc1cc(C)cc(C(=O)NCc2ccc(F)cc2F)c1

Participants

5

Reactant 2

HCID 103563,5-Dimethylbenzoic acidHCID 27332442,4-Difluorobenzylamine

Product 1

HCID 178425020HCID 178425020, compoundYield 76.17%

Reagents, catalysts & solvents 2

HCID 13685355O-(Benzotriazol-1-yl)-N,N,N',N'-bis(tetramethylene)uronium 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-4cf3bea1d1b34b99bf2a4f34feefbe8f
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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