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

HRID 69967

反応式

HRID 69967 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-99c3dfecc6454d368e50018cc0841db2
出典データセット
uspto-grants-2014_09
特許番号
US08822497B2

関連ノート

読み込み中…