Butylamine → HCID 62233980, compound

HRID 530445Notes

Reaction equation

HRID 530445 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.Cl.[CH2:23]([NH2:27])[CH2:24][CH2:25][CH3:26]>C(Cl)Cl>[CH2:23]([NH:27][C:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[N:7]=1)=[O:10])[CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 8007ButylamineHCID 208126-Chloropicolinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 62233980HCID 62233980, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Chloro-pyridine-2-carboxylic acid (500 mg, 3.17 mmol), EDC.HCl (1.34 g, 6.98 mmol) and HOBN (1.42 g, 7.93 mmol) were dissolved in DCM (30 mL) and NEM (914 mg, 7.93 mmol) and n-butylamine (376 μL, 3.81 mmol) were added. The reaction mixture was stirred for 16 h, washed with sat aq NaHCO3 (2×20 mL), 1 M aq HCl (2×20 mL), brine (20 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography to give the title compound (321 mg, 48%) as a colourless liquid. LCMS (ES+): 213.5 [MH]+.

Workup

  1. washwashed with sat aq NaHCO3 (2×20 mL), 1 M aq HCl (2×20 mL), brine (20 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c0da86ec222c47aabf325fd2d0feba7f
Source dataset
uspto-grants-2016_05
Patent number
US09353086B2

Reaction notes

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