Cyclopropanemethanamine → HCID 86700707, compound

HRID 530452Notes

Reaction equation

HRID 530452 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[C:5]([CH3:11])=[CH:4][CH:3]=1.[NH2:12][CH2:13][CH:14]1[CH2:16][CH2:15]1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([NH:12][CH2:13][CH:14]2[CH2:16][CH2:15]2)=[O:10])[C:5]([CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 75646CyclopropanemethanamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 469414706-Chloro-3-methylpyridine-2-carboxylic acid

Product 1

HCID 86700707HCID 86700707, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Chloro-3-methylpyridine-2-carboxylic acid (595 mg, 3.47 mmol), aminomethylcyclopropane (356 μL, 4.16 mmol), EDC.HCl (1.46 g, 7.63 mmol), HOBN (1.54 g, 8.67 mmol) and NEM (1.10 mL, 8.67 mmol) were dissolved in DCM (30 mL) and stirred for 16 h. The reaction mixture was washed with sat aq NaHCO3 (30 mL), 1M aq HCl (30 mL), brine (30 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography to give the title compound (215 mg, 28%) as a yellow solid. LCMS (ES+): 225.5 [MH]+.

Workup

  1. washThe reaction mixture was washed with sat aq NaHCO3 (30 mL), 1M aq HCl (30 mL), brine (30 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ddb72c04628545b58ab91d35d937ada7
Source dataset
uspto-grants-2016_05
Patent number
US09353086B2

Reaction notes

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