6-Chloropicolinic acid → HCID 55052394, compound

HRID 530446Notes

Reaction equation

HRID 530446 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.[CH3:21][CH2:22][N:23]=[C:24]=[N:25][CH2:26][CH2:27][CH2:28][N:29](C)C.Cl.NCCCN1C=CN=C1>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([NH:29][CH2:28][CH2:27][CH2:26][N:25]2[CH:21]=[CH:22][N:23]=[CH:24]2)=[O:10])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 208126-Chloropicolinic acidHCID 757711-HydroxybenzotriazoleHCID 787361H-Imidazole-1-propanamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 55052394HCID 55052394, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6-Chloro-pyridine-2-carboxylic acid (1.00 g, 6.35 mmol) was dissolved in DCM (20 mL) and HOBt (1.03 g, 7.62 mmol), EDC.HCl (1.46 g, 7.62 mmol) and 1-(3-aminopropyl)imidazole (0.95 g, 7.62 mmol) were added. The reaction mixture was stirred for 18 h, diluted with DCM (130 mL) washed with sat aq Na2CO3 (100 mL), brine (30 mL), water (30 mL), dried (MgSO4) and concentrated in vacuo. The residue was triturated with water to give the crude title compound (1.05 g, 63%) as an off-white solid. LCMS (ES+): 266 [MH]+.

Workup

  1. washwashed
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated with water

Sources & evidence

ORD record
ord-8b39532c93934df093a5c6672e88ab20
Source dataset
uspto-grants-2016_05
Patent number
US09353086B2

Reaction notes

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