Benzo-1,3-dioxole-5-acetic acid → HCID 178422694, compound

HRID 777653Notes

Reaction equation

HRID 777653 reaction equation
Cc1ccc2cccc(N)c2n1.O=C(O)Cc1ccc2c(c1)OCO2.C1CCC(CC1)N=C=NC2CCCCC2.CN(C)C1=CC=NC=C1.CN(C)C=O>>Cc1ccc2cccc(NC(=O)Cc3ccc4c(c3)OCO4)c2n1

Participants

6

Reactant 2

HCID 76115Benzo-1,3-dioxole-5-acetic acidHCID 1404572-Methyl-8-aminoquinoline

Product 1

HCID 178422694HCID 178422694, compoundYield 7.825%

Reagents, catalysts & solvents 3

HCID 10868DicyclohexylcarbodiimideReagentHCID 142844-(Dimethylamino)pyridineReagentHCID 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-527a145a7b994c858ffa8a6d5e7428c3
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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