1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 57786334, compound

HRID 1628613Notes

Reaction equation

HRID 1628613 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]1[C:15]2=[N:16][C:17]3[C:22]([Cl:23])=[CH:21][CH:20]=[C:19]([CH:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[C:18]=3[N:14]2[CH2:13][CH2:12]1)[C:5]([OH:7])=O.[NH4+].O[N:31]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]1[C:15]2=[N:16][C:17]3[C:22]([Cl:23])=[CH:21][CH:20]=[C:19]([CH:24]([CH2:25][CH3:26])[CH2:27][CH3:28])[C:18]=3[N:14]2[CH2:13][CH2:12]1)[C:5]([NH2:31])=[O:7]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220338091-Hydroxybenzotriazole, ammonium saltHCID 57786316HCID 57786316, compound

Product 1

HCID 57786334HCID 57786334, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-chloro-4-[8-chloro-5-(1-ethylpropyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-1-yl]benzoic acid (45.4 mg, 0.109 mmol) in N,N-dimethylformamide (1.0 mL) were added 1-hydroxy-1H-benzotriazole ammonium salt (21.4 mg, 0.141 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (22.9 mg, 0.119 mmol). The reaction mixture was stirred at room temperature for 8 hr. The reaction mixture was quenched with aqueous saturated sodium hydrogen carbonate and extracted with ethyl acetate (×3). The combined organic layer was washed with water (×2), aqueous saturated sodium hydrogen carbonate (×1) and brine (×1), dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was recrystallized from ethyl acetate/n-hexane to give the title compound as a colorless solid (36.4 mg, 0.0872 mmol, 80%).

Workup

  1. customThe reaction mixture was quenched with aqueous saturated sodium hydrogen carbonate
  2. extractionextracted with ethyl acetate (×3)
  3. washThe combined organic layer was washed with water (×2), aqueous saturated sodium hydrogen carbonate (×1) and brine (×1)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-ac99542e4b104ffaac00ab7e36f82c87
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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