Propionic Acid → N-(3-chloro-4-(4-propionylpiperazin-1-yl)phenyl)picolinamide

HRID 38253Notes

Reaction equation

HRID 38253 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:14][C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.[C:23](O)(=[O:26])[CH2:24][CH3:25].CCN=C=NCCCN(C)C.Cl.CCN(CC)CC.OC1C2N=NNC=2C=CC=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:14][C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:23](=[O:26])[CH2:24][CH3:25])[CH2:10][CH2:9]1

Participants

7

Reactant 5

HCID 1032Propionic AcidHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67441344N-(3-chloro-4-(piperazin-1-yl)phenyl)picolinamideHCID 178418300HCID 178418300, compound

Product 1

HCID 42645243N-(3-chloro-4-(4-propionylpiperazin-1-yl)phenyl)picolinamideYield 73.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to Scheme 5 Step 5 Method A: A solution of N-(3-chloro-4-(piperazin-1-yl)phenyl)picolinamide (0.19 mmol, 60 mg), propionic acid (0.19 mmol, 14 μL), EDCI.HCl (0.28 mmol, 54 mg), Et3N (0.38 mmol, 53 μL) and of hydroxybenzotriazole (0.21 mmol, 32 mg) in DCM (5 mL) was stirred at room temperature for 1 day. The solution was quenched with water. The aqueous phase was extracted with DCM. The organic phase was washed with brine, was dried over Na2SO4, was filtered and was concentrated under reduced pressure. The solid was triturated with water and finally with iPr2O to afford N-(3-chloro-4-(4-propionylpiperazin-1-yl)phenyl)picolinamide (0.14 mmol, 51 mg, 72%) as a yellow solid.

Workup

  1. customThe solution was quenched with water
  2. extractionThe aqueous phase was extracted with DCM
  3. washThe organic phase was washed with brine
  4. dry with materialwas dried over Na2SO4
  5. filtrationwas filtered
  6. concentrationwas concentrated under reduced pressure
  7. customThe solid was triturated with water and finally with iPr2O

Sources & evidence

ORD record
ord-b6c6bdf7a979439097c74dd627070f92
Source dataset
uspto-grants-2013_09
Patent number
US08524726B2

Reaction notes

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