Oxalyl chloride → HCID 86700710, compound

HRID 530462Notes

Reaction equation

HRID 530462 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[C:4]([CH3:11])[CH:3]=1.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C.[NH2:27][CH2:28][CH:29]1[CH2:31][CH2:30]1>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([NH:27][CH2:28][CH:29]2[CH2:31][CH2:30]2)=[O:10])[CH:5]=[C:4]([CH3:11])[CH:3]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 75646CyclopropanemethanamineHCID 81531DiisopropylethylamineHCID 230023816-Chloro-4-methylpyridine-2-carboxylic acid

Product 1

HCID 86700710HCID 86700710, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

6-Chloro-4-methylpyridine-2-carboxylic acid (422 mg, 2.46 mmol) was dissolved in DCM (10 mL) and oxalyl chloride (422 μL, 4.92 mmol) and DMF (100 μL) were added. The reaction mixture was stirred for 3 h, the solvents were removed in vacuo and the residue was azeotroped with DCM. The residue was dissolved in DCM (10 mL), DIPEA (1.63 mL, 9.84 mmol) and aminomethylcyclopropane (427 μL, 4.92 mmol) were added and the reaction mixture was stirred for 1 h. The reaction mixture was diluted with DCM (40 mL), washed with sat aq NaHCO3 (50 mL), 1 M aq HCl (50 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography to give the title compound (494 mg, 69%) as a yellow liquid. LCMS (ES+): 225.5 [MH]+.

Workup

  1. customthe solvents were removed in vacuo
  2. customthe residue was azeotroped with DCM
  3. dissolutionThe residue was dissolved in DCM (10 mL)
  4. stirringthe reaction mixture was stirred for 1 h
  5. washwashed
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-dc3966bf90304cfd829cb466e3771bf1
Source dataset
uspto-grants-2016_05
Patent number
US09353086B2

Reaction notes

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