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

HRID 69967

Reaction equation

HRID 69967 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-99c3dfecc6454d368e50018cc0841db2
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Linked notes

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