Isonicotinic Acid → HCID 23144216, compound

HRID 337486Notes

Reaction equation

HRID 337486 reaction equation
[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][CH:6]([C:9]([C:11]2[S:15][C:14]([NH2:16])=[N:13][C:12]=2[C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)=[O:10])[CH2:5][CH2:4]1.[C:22](O)(=[O:29])[C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1.CCN=C=NCCCN(C)C.Cl.O.ON1C2C=CC=CC=2N=N1>C1COCC1.O>[O:18]1[CH:19]=[CH:20][CH:21]=[C:17]1[C:12]1[N:13]=[C:14]([NH:16][C:22]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)=[O:29])[S:15][C:11]=1[C:9]([CH:6]1[CH2:5][CH2:4][CH:3]([O:2][CH3:1])[CH2:8][CH2:7]1)=[O:10]

Participants

7

Reactant 4

HCID 5922Isonicotinic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 86060955HCID 86060955, compound

Product 1

HCID 23144216HCID 23144216, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Compound 441 (579 mg, 1.89 mmol) was dissolved in THF (9.0 mL), and isonicotinic acid (931 mg, 7.57 mmol), EDC hydrochloride (1.45 g, 7.57 mmol) and 1-hydroxybenzotriazole monohydrate (1.16 g, 7.57 mmol) were added thereto, followed by stirring at 60° C. for 3 hours. The reaction mixture was poured into water, 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 2-propanol to afford the entitled Compound 442 (664 mg, 85%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe resulting residue was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-40d0bcc0e04f44a582a0fb9c3b3f88fc
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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