Pyridine → HCID 22709993, compound

HRID 352910Notes

Reaction equation

HRID 352910 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:34])[C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=4)=[CH:24][CH:23]=3)[CH:17]([C:35]([O:37]CC)=O)[CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.[N:55]1C=CC=CC=1.C(=O)(O)[O-].[NH4+]>CN(C)C=O>[ClH:1].[C:35]([CH:17]1[CH2:16][N:15]([S:12]([C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=3)[CH:8]=2)(=[O:14])=[O:13])[CH2:20][CH2:19][N:18]1[C:21](=[O:34])[C:22]1[CH:23]=[CH:24][C:25]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)=[CH:26][CH:27]=1)(=[O:37])[NH2:55]

Participants

6

Reactant 4

HCID 1049PyridineHCID 14013Ammonium BicarbonateHCID 90495Di-tert-butyl dicarbonateHCID 22709459HCID 22709459, compound

Product 1

HCID 22709993HCID 22709993, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In the same manner as in Example A-3, with 4-[(6-chloronaphthalen-2-yl)sulfonyl]-2-ethoxycarbonyl-1-[4-(pyridin-3-yl)benzoyl]piperazine (426 mg) as a starting material, a crude product was obtained by the hydrolysis of the ester, followed by suspension in N,N-dimethylformamide (35 ml). Under ice cooling, di-tert-butyl dicarbonate (646 mg), pyridine (370 μl) and ammonium bicarbonate (196 mg) were added to the resulting suspension. The resulting mixture was stirred at room temperature for 19 hours. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (4% methanol—dichloromethane) and the eluate was dissolved in tetrahydrofuran. Solution of hydrochloride in ethanol was added to the resulting solution to solidify the same. The resulting solid was collected by filtration and dissolved in a mixed solvent of water and methanol. The insoluble matter was filtered off and the filtrate was distilled under reduced pressure, whereby the title compound (302 mg, 65%) was obtained.

Workup

  1. customThe residue obtained
  2. distillationby distilling off the solvent under reduced pressure
  3. customwas purified by chromatography on a silica gel column (4% methanol—dichloromethane)
  4. dissolutionthe eluate was dissolved in tetrahydrofuran
  5. additionSolution of hydrochloride in ethanol was added to the resulting solution
  6. filtrationThe resulting solid was collected by filtration
  7. dissolutiondissolved in a mixed solvent of water and methanol
  8. filtrationThe insoluble matter was filtered off
  9. distillationthe filtrate was distilled under reduced pressure, whereby the title compound (302 mg, 65%)
  10. customwas obtained

Sources & evidence

ORD record
ord-0d38d48f333a4fe3bb631197976a34df
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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