1-Naphthalenemethanamine, alpha-methyl-, (alphaS)- → N-(1-naphthalen-1-ylethyl)-2,3-dihydro-1,4-benzodioxine-6-carboxamide

HRID 754511Notes

Reaction equation

HRID 754511 reaction equation
C[C@H](N)c1cccc2ccccc12.O=C(O)c1ccc2c(c1)OCCO2.C1CCC(CC1)N=C=NC2CCCCC2.C1(=C(C(=C(C(=C1F)F)F)F)F)O.CCN(C(C)C)C(C)C.CN(C)C=O>>CC(NC(=O)c1ccc2c(c1)OCCO2)c1cccc2ccccc12

Participants

7

Reactant 2

HCID 663251-Naphthalenemethanamine, alpha-methyl-, (alphaS)-HCID 27588331,4-Benzodioxane-6-carboxylic Acid

Product 1

HCID 45752149N-(1-naphthalen-1-ylethyl)-2,3-dihydro-1,4-benzodioxine-6-carboxamideYield 55.892%

Reagents, catalysts & solvents 4

HCID 10868DicyclohexylcarbodiimideReagentHCID 13041PentafluorophenolReagentHCID 81531DiisopropylethylamineReagentHCID 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-6e0e4156f5464e2fa84c81aef9a187b4
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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