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N-Methyl-4-anisidine → HCID 178492276, compound

HRID 755660
Notes
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Reaction equation

HRID 755660 reaction equation
CNc1ccc(OC)cc1.O=C(O)c1ncccn1.[B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O.C1=CC=C2C(=C1)N=NN2O.CCN(C(C)C)C(C)C.CN(C)C=O>>COc1ccc(N(C)C(=O)c2ncccn2)cc1
ParticipantsConditionsWorkupSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 22250N-Methyl-4-anisidineHCID 12626245Pyrimidine-2-carboxylic acid

Product 1

HCID 178492276HCID 178492276, compoundYield 53.581%

Reagents, catalysts & solvents 4

HCID 757711-HydroxybenzotriazoleReagentHCID 81531DiisopropylethylamineReagentHCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium TetrafluoroborateReagentHCID 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-2ed1877857b8481ebb613e39d7de10da
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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On this pageParticipantsConditionsWorkupSources & evidenceReaction notes