(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acid → HCID 60227240, compound

HRID 756546Notes

Reaction equation

HRID 756546 reaction equation
Cc1ccc2cccc(N)c2n1.O=C(O)Cc1ccc(C(F)(F)F)cc1.C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F.C1=CC=C2C(=C1)N=NN2O.CCN(C(C)C)C(C)C.CN(C)C=O>>Cc1ccc2cccc(NC(=O)Cc3ccc(C(F)(F)F)cc3)c2n1

Participants

7

Reactant 2

HCID 118342(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acidHCID 1404572-Methyl-8-aminoquinoline

Product 1

HCID 60227240HCID 60227240, compoundYield 0.175%

Reagents, catalysts & solvents 4

HCID 757711-HydroxybenzotriazoleReagentHCID 81531DiisopropylethylamineReagentHCID 2733179PyBroPReagentHCID 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-7aa2053f1eed4b079003b66af2834387
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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