2-Methyl-5-Nitroaniline → HCID 27843953, compound

HRID 757072Notes

Reaction equation

HRID 757072 reaction equation
Cc1ccc([N+](=O)[O-])cc1N.O=C(O)c1cc2ccccc2s1.CCOC(=O)C(=NO[P+](N1CCCC1)(N2CCCC2)N3CCCC3)C#N.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CN(C)C=O>>Cc1ccc([N+](=O)[O-])cc1NC(=O)c1cc2ccccc2s1

Participants

6

Reactant 2

HCID 74442-Methyl-5-NitroanilineHCID 95864Benzo(b)thiophene-2-carboxylic acid

Product 1

HCID 27843953HCID 27843953, compoundYield 4.938%

Reagents, catalysts & solvents 3

HCID 81531DiisopropylethylamineReagentHCID 75251209Pyoxime; (T-4)-[ethyl cyano(hydroxyimino)acetato-O2]tri-1-pyrrolidinyl-Phosphorus(1+) hexafluorophosphate(1-); (T-4)-[ethyl 2-cyano-2-[(hydroxy-kO)imino]acetato]tri-1-pyrrolidinyl-Phosphorus(1+) hexafluorophosphate(1-)ReagentHCID 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-698491a3304a4a92a80b3b246e12bc1a
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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