1,2-Dichloroethane → 3-amino-N-(4-chloropyridin-3-yl)-6-(2,6-difluorophenyl)picolinamide

HRID 69967

반응식

HRID 69967 반응식
[NH2:1][C:2]1[C:3]([C:16]([OH:18])=O)=[N:4][C:5]([C:8]2[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=2[F:15])=[CH:6][CH:7]=1.[Cl:19][C:20]1[CH:25]=[CH:24][N:23]=[CH:22][C:21]=1[NH2:26].C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl.CCOC(C)=O.O>[NH2:1][C:2]1[C:3]([C:16]([NH:26][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][C:20]=2[Cl:19])=[O:18])=[N:4][C:5]([C:8]2[C:9]([F:15])=[CH:10][CH:11]=[CH:12][C:13]=2[F:14])=[CH:6][CH:7]=1

참가 물질

8

반응물 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 5819323-Amino-4-chloropyridineHCID 592264283-Amino-6-(2,6-difluorophenyl)picolinic acid

생성물 1

HCID 690428363-amino-N-(4-chloropyridin-3-yl)-6-(2,6-difluorophenyl)picolinamide수율 21%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 3-amino-6-(2,6-difluorophenyl)picolinic acid (1.0 equiv.), 4-chloropyridin-3-amine (2.0 equiv.), HOAt (1.0 equiv.), and EDC (1.0 equiv.) in DCM at a concentration of (0.2M) was stirred for 24 hr. Water was added to the reaction, followed by EtOAc. The organic layer was separated, dried with brine, MgSO4, and concentrated. The crude material was purified via SiO2 column chromatography eluting with EtOAc and hexanes (1:1) to give the product as a light yellow solid (21% yield). LCMS (m/z): 361.1 (MH+); LC Rt=3.28 min.

후처리

  1. customThe organic layer was separated
  2. dry with materialdried with brine, MgSO4
  3. concentrationconcentrated
  4. customThe crude material was purified via SiO2 column chromatography
  5. washeluting with EtOAc and hexanes (1:1)

출처 및 근거

ORD 기록
ord-99c3dfecc6454d368e50018cc0841db2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822497B2

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