Hydrochloric Acid → HCID 67078752, compound

HRID 338612Notes

Reaction equation

HRID 338612 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7](=[CH2:11])C(O)=O)[CH:2]=1.[CH3:12][N:13]([C:15]([O:19]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.N[C:44]1[CH:52]=[CH:51][C:47]([C:48]([OH:50])=[O:49])=[CH:46][CH:45]=1.Cl>[OH-].[Na+].C(#N)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[CH:11][C:15]([NH:13][CH2:12][C:44]2[CH:52]=[CH:51][C:47]([C:48]([OH:50])=[O:49])=[CH:46][CH:45]=2)=[O:19])[CH:2]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 9784-Aminobenzoic AcidHCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 18952396HCID 18952396, compound

Product 1

HCID 67078752HCID 67078752, compoundYield 67.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 14798Sodium HydroxideSolvent

Procedure

Dissolving 3-pyridylacrylic acid (1.49 g, 10 mmol) and HBTU (3.79 g, 10 mmol) into 10 ml of acetonitrile, drop-adding triethylamine (2.02 g, 20 mmol), stirring at room temperature 30 minutes, to obtain a yellow sticky liquid. Dissolving p-aminobenzoic acid (1.52 g, 10 mmol) in 10 ml of 1 mol/L sodium hydroxide aqueous solution, and thereto drop-adding the above yellow sticky liquid at 60° C. After completion of drop-addition, maintaining the temperature for 1 hour to complete the reaction. The reaction solution is adjusted to pH of about 7 with concentrated hydrochloric acid. Large amount of solids are precipitated, filtrated and dried to obtain 1.90 g of 4-[(3-pyridylacryloyl)aminomethyl]benzoic acid (intermediate M-20) as a white solid, with a yield of 67.6%.

Workup

  1. customto obtain a yellow sticky liquid
  2. additionAfter completion of drop-addition
  3. temperaturemaintaining the temperature for 1 hour
  4. customthe reaction
  5. customLarge amount of solids are precipitated
  6. filtrationfiltrated
  7. customdried

Sources & evidence

ORD record
ord-c0c404799020498c9171f27fbbb7454d
Source dataset
uspto-grants-2014_11
Patent number
US08889876B2

Reaction notes

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