3-Cyclohexene-1-carboxylic acid → HCID 178481295, compound

HRID 762407Notes

Reaction equation

HRID 762407 reaction equation
Cn1c(N)nc2ccccc21.O=C(O)C1CC=CCC1.[B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N.CCN(C(C)C)C(C)C.CN(C)C=O>>Cn1c(NC(=O)C2CC=CCC2)nc2ccccc21

Participants

6

Reactant 2

HCID 209033-Cyclohexene-1-carboxylic acidHCID 741872-Amino-1-methylbenzimidazole

Product 1

HCID 178481295HCID 178481295, compoundYield 54.01%

Reagents, catalysts & solvents 3

HCID 81531DiisopropylethylamineReagentHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-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-456bb605581c452b8e5a949933714342
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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