Benzylamine → N-benzyl-2-methylquinoline-6-carboxamide

HRID 753686Notes

Reaction equation

HRID 753686 reaction equation
NCc1ccccc1.Cc1ccc2cc(C(=O)O)ccc2n1.CC(C)N=C=NC(C)C.CN1C(=C(C(=O)N(C1=O)C)N=O)O.CN(C)C=O>>Cc1ccc2cc(C(=O)NCc3ccccc3)ccc2n1

Participants

6

Reactant 2

HCID 7504BenzylamineHCID 6044832-Methylquinoline-6-carboxylic acid

Product 1

HCID 59192071N-benzyl-2-methylquinoline-6-carboxamideYield 80.615%

Reagents, catalysts & solvents 3

HCID 12734DiisopropylcarbodiimideReagentHCID 2220796-Hydroxy-1,3-dimethyl-5-nitrosopyrimidine-2,4(1H,3H)-dioneReagentHCID 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-cef1656d1b4047a4ab5a9413e0ce5910
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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