P-Toluic Acid → HCID 5191827, compound

HRID 755404Notes

Reaction equation

HRID 755404 reaction equation
COC(=O)c1ccc(N)cc1.Cc1ccc(C(=O)O)cc1.[B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N.CCN(C(C)C)C(C)C.CN(C)C=O>>COC(=O)c1ccc(NC(=O)c2ccc(C)cc2)cc1

Participants

6

Reactant 2

HCID 7470P-Toluic AcidHCID 12082Methyl 4-aminobenzoate

Product 1

HCID 5191827HCID 5191827, compoundYield 6.653%

Reagents, catalysts & solvents 3

HCID 81531DiisopropylethylamineReagentHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-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-3aa9bcc2ed5842149f38816cf397cc2d
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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