1,3-Propanediamine → HCID 58726834, compound

HRID 502601Notes

Reaction equation

HRID 502601 reaction equation
Br[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[S:4][N:3]=1.[NH2:11][CH2:12][CH2:13][CH2:14][NH2:15]>CO.C(OCC)(=O)C>[S:4]1[C:5]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[C:2]([NH:11][CH2:12][CH2:13][CH2:14][NH2:15])=[N:3]1

Participants

5

Reactant 2

HCID 4281,3-PropanediamineHCID 57436558HCID 57436558, compound

Product 1

HCID 58726834HCID 58726834, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Bromoisothiazolo[4,5-b]pyridine (1.90 g, 8.8 mmol) and 1,3-diaminopropane (6.70 g, 90 mmol) in methanol (15 ml) was heated at 64° C. for 1.5 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The crude reaction mixture was diluted with ethyl acetate and washed successively with saturated aqueous sodium bicarbonate solution and brine. The organic solution was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Lyophilization of the crude sample in acetonitrile/water yielded N1-(isothiazolo[4,5-b]pyridin-3-yl)propane-1,3-diamine. 1H NMR (300 MHz, DMSO-d6): 8.55 (d, 1H), 8.05 (d, 1H), 7.32 (dd, 1H), 6.25 (br s, 1H), 3.65 (m, 2H), 2.85 (t, 2H), 1.85 (t, 2H), 1.45 ppm (br s, 2H). MW=208 confirmed by LC-MS, tr=5.91 min (Method Y) MH+=209.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude reaction mixture
  3. washwashed successively with saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-41c39a68637c44049ebb749b9f398a15
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

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