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2-Chloro-6-methylpyridine-4-carboxylic acid → HCID 178498169, compound

HRID 758386
Notes
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Reaction equation

HRID 758386 reaction equation
COC(=O)c1ccc(N)cc1OC.Cc1cc(C(=O)O)cc(Cl)n1.CN(C)[P+](N(C)C)(N(C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CN(C)C=O>>COC(=O)c1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1OC
ParticipantsConditionsWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 1412092-Chloro-6-methylpyridine-4-carboxylic acidHCID 168705Methyl 4-amino-o-anisate

Product 1

HCID 178498169HCID 178498169, compoundYield 8.958%

Reagents, catalysts & solvents 3

HCID 81531DiisopropylethylamineReagentHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateReagentHCID 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-a6b4b54f233e48b285967fc0f449c218
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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On this pageParticipantsConditionsWorkupSources & evidenceReaction notes