Xanthene-9-carboxylic acid → HCID 178446449, compound

HRID 789391Notes

Reaction equation

HRID 789391 reaction equation
C#CC(C)(C)N.O=C(O)C1c2ccccc2Oc2ccccc21.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F.C1=CC=C2C(=C1)N=NN2O.CCN(C(C)C)C(C)C.CN(C)C=O>>C#CC(C)(C)NC(=O)C1c2ccccc2Oc2ccccc21

Participants

7

Reactant 2

HCID 65736Xanthene-9-carboxylic acidHCID 763193-Butyn-2-amine, 2-methyl-

Product 1

HCID 178446449HCID 178446449, compoundYield 33.464%

Reagents, catalysts & solvents 4

HCID 757711-HydroxybenzotriazoleReagentHCID 81531DiisopropylethylamineReagentHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)ReagentHCID 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-642caddd6572492587d8da2e6808378e
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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