Cyclopropanemethanamine → HCID 68278671, compound

HRID 530461Notes

Reaction equation

HRID 530461 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([OH:9])=O)[N:6]=1.[NH2:10][CH2:11][CH:12]1[CH2:14][CH2:13]1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[Br:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([NH:10][CH2:11][CH:12]2[CH2:14][CH2:13]2)=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 75646CyclopropanemethanamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27632092-Bromo-1,3-thiazole-4-carboxylic acid

Product 1

HCID 68278671HCID 68278671, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Bromothiazole-4-carboxylic acid (500 mg, 2.40 mmol), aminomethylcyclopropane (247 μL, 2.88 mmol), EDC.HCl (1.01 g, 5.29 mmol), HOBN (1.08 g, 6.01 mmol) and NEM (765 μL, 6.01 mmol) were dissolved in DCM (30 mL) and the reaction mixture was stirred for 16 h. The organic fraction was washed with sat aq NaHCO3 (30 mL), 1 M aq HCl (30 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography to give the title compound (404 mg, 64%) as a white solid. LCMS (ES+): 261.4 [MH]+.

Workup

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

Sources & evidence

ORD record
ord-ddccc82f84f64f11aae36c2e5a517ee6
Source dataset
uspto-grants-2016_05
Patent number
US09353086B2

Reaction notes

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