Nicotinic Acid → HCID 12971776, compound

HRID 2185799Notes

Reaction equation

HRID 2185799 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.[NH2:22][C:23]1[CH:48]=[CH:47][C:26]([CH2:27][N:28]2[C:33](=[O:34])[C:32]([C:35]([O:37][CH3:38])=[O:36])=[CH:31][C:30]([C:39]3[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=3)=[N:29]2)=[CH:25][CH:24]=1>O1CCCC1>[CH3:38][O:37][C:35]([C:32]1[C:33](=[O:34])[N:28]([CH2:27][C:26]2[CH:25]=[CH:24][C:23]([NH:22][C:1]([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=3)=[O:9])=[CH:48][CH:47]=2)[N:29]=[C:30]([C:39]2[CH:40]=[CH:41][C:42]([O:45][CH3:46])=[CH:43][CH:44]=2)[CH:31]=1)=[O:36]

Participants

5

Reactant 3

HCID 938Nicotinic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12971775HCID 12971775, compound

Product 1

HCID 12971776HCID 12971776, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of nicotinic acid (38 mg, 0.31 mmol) in tetrahydrofuran (2 ml), N-[3-(dimethylamino)-propyl]-N′-ethylcarbodiimide.hydrochloride (WSC.HCl) (60 mg,0.31 mmol) was added at room temperature, followed by stirring for 5 minutes. A solution of 2-(4-aminobenzyl)-4-methoxycarbonyl-6-(4-methoxyphenyl)-2H-pyridazin-3-one (76 mg, 0.21 mmol) in tetrahydrofuran (2 ml) was then added, followed by stirring at the same temperature for 13 hours. The solvent was distilled off under reduced pressure, and the residue was dissolved in chloroform (30 ml). The solution was washed successively with water (30 ml) and a saturated aqueous solution of sodium chloride (brine) (30 ml), and was then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was separated and purified by silica gel preparative chromatography [developer: chloroform/methanol (10/1)], followed by crystallization from chloroform-hexane. The title compound (78 mg, 79.7%) was obtained as yellow prisms.

Workup

  1. additionwas added at room temperature
  2. stirringby stirring at the same temperature for 13 hours
  3. distillationThe solvent was distilled off under reduced pressure
  4. dissolutionthe residue was dissolved in chloroform (30 ml)
  5. washThe solution was washed successively with water (30 ml)
  6. dry with materiala saturated aqueous solution of sodium chloride (brine) (30 ml), and was then dried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue was separated
  9. custompurified by silica gel preparative chromatography [developer: chloroform/methanol (10/1)]
  10. customfollowed by crystallization from chloroform-hexane

Sources & evidence

ORD record
ord-7a5f00d5dfa94d6a9cbee389bb407635
Source dataset
uspto-grants-2002_06
Patent number
US06403586B1

Reaction notes

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