Propylamine → HCID 178446867, compound

HRID 892124Notes

Reaction equation

HRID 892124 reaction equation
Cl.[CH2:2]([C@@H:9]1[CH2:20][N:19]2[C:11]([C:12]3[NH:13][C:14]([CH:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)=[N:15][C:16]=3[N:17]([CH2:22][C:23]([OH:25])=O)[C:18]2=[O:21])=[N:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:31](N)[CH2:32][CH3:33].Cl.C([N:38]=C=NCCCN(C)C)C>O.O1CCOCC1>[CH2:2]([C@@H:9]1[CH2:20][N:19]2[C:11]([C:12]3[NH:13][C:14]([CH:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)=[N:15][C:16]=3[N:17]([CH:22]([CH2:31][CH2:32][CH3:33])[C:23]([NH2:38])=[O:25])[C:18]2=[O:21])=[N:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 7852PropylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178479764HCID 178479764, compound

Product 1

HCID 178446867HCID 178446867, compoundYield 45.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Compound 77(50 mg, 0.127 mmol) obtained in Example 77 was dissolved in water (1 mL) and 1,4-dioxane (1 mL), to the solution were added n-propylamine (14 μL, 0.176 mmol, 1.4 equivalents) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (24 mg, 0.127 mmol, 1.0 equivalent), and the mixture was stirred at room temperature for 4 days. The reaction solution was extracted with chloroform, and the extract was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (chloroform:methanol=98:2 to 90:10) to obtain the title compound (25 mg, 45%).

Workup

  1. extractionThe reaction solution was extracted with chloroform
  2. washthe extract was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (chloroform:methanol=98:2 to 90:10)

Sources & evidence

ORD record
ord-f50ee8462e3d45f49e3848992852fd6d
Source dataset
uspto-grants-2006_02
Patent number
US07005430B2

Reaction notes

Loading…