Isonicotinic Acid → HCID 23144127, compound

HRID 337479Notes

Reaction equation

HRID 337479 reaction equation
[C:1]([C:5]([C:7]1[S:11][C:10]([NH2:12])=[N:9][C:8]=1[C:13]1[O:14][CH:15]=[CH:16][CH:17]=1)=[O:6])([CH3:4])([CH3:3])[CH3:2].[C:18](O)(=[O:25])[C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1.CCN=C=NCCCN(C)C.Cl.O.ON1C2C=CC=CC=2N=N1>CN(C=O)C>[O:14]1[CH:15]=[CH:16][CH:17]=[C:13]1[C:8]1[N:9]=[C:10]([NH:12][C:18]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)=[O:25])[S:11][C:7]=1[C:5](=[O:6])[C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 5922Isonicotinic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 23144700HCID 23144700, compound

Product 1

HCID 23144127HCID 23144127, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Compound 399 (102 mg, 0.408 mmol) was dissolved in DMF (5 mL), and isonicotinic acid (199 mg, 1.63 mmol), EDC hydrochloride (309 mg, 1.61 mmol) and 1-hydroxybenzotriazole monohydrate (245 mg, 1.60 mmol) were added thereto, followed by stirring at 60° C. for 1.5 hours. The reaction mixture was concentrated under reduced pressure, and a saturated aqueous solution of sodium hydrogencarbonate was added to the resulting residue, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was recrystallized from ethanol to afford the entitled Compound 400 (115 mg, 79%) as a pale yellowish green solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona saturated aqueous solution of sodium hydrogencarbonate was added to the resulting residue
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled away under reduced pressure
  7. customThe resulting residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-6f68bb3500844f23a16a2f90f65f1ef1
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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