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

HRID 38253노트

반응식

HRID 38253 반응식
[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

참가 물질

7

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b6c6bdf7a979439097c74dd627070f92
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524726B2

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