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4-Aminopyridine → 2-{4-[2-(3,5-Dimethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-N-pyridin-4-yl-benzamide

HRID 1810958
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HRID 1810958 반응식
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([CH2:8][C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=3[C:19](O)=[O:20])[CH2:13][CH2:12]2)=[O:10])[N:3]=1.C(Cl)(=O)C(Cl)=O.[NH2:32][C:33]1[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.CN(C=O)C>[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([CH2:8][C:9]([N:11]2[CH2:12][CH2:13][N:14]([C:17]3[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=3[C:19]([NH:32][C:33]3[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=3)=[O:20])[CH2:15][CH2:16]2)=[O:10])[N:3]=1
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참가 물질

7

반응물 4

HCID 17274-AminopyridineHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 57516317{4-[2-(3,5-Dimethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-benzoic acid

생성물 1

HCID 595488082-{4-[2-(3,5-Dimethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-N-pyridin-4-yl-benzamide수율 63%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
촉매
HCID 6344Dichloromethane용매

실험 절차

To 2-{4-[2-(3,5-dimethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-benzoic acid (0.051 g, 0.150 mmol) in 2 mL of CH2Cl2 at 4° C. is added 2 M oxalyl chloride solution (0.100 mL, 0.200 mmol) and 2 drops of dry DMF. The mixture is allowed to warm to room temperature over 1 h. To this is added 4-aminopyridine in one portion and diisopropylethyl amine (0.100 mL, 0.310 mmol). The mixture is stirred for 16 h. The mixture is concentrated and then purified via preparative HPLC (20-80% CH3CN/H2O). The product is further purified using a SiO2 prep-plate, eluting with (10% MeOH/CH2Cl2) to give 0.032 g of the title compound in 63% yield. MS MH+=419.2

후처리

  1. concentrationThe mixture is concentrated
  2. custompurified via preparative HPLC (20-80% CH3CN/H2O)
  3. customThe product is further purified
  4. washeluting with (10% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-7d4bccab19574f75a4a8743ff6dfdf88
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08362249B2

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