1,3-Propanediamine → N1-(isothiazolo[5,4-b]pyrazin-3-yl)propane-1,3-diamine

HRID 502572Notes

Reaction equation

HRID 502572 reaction equation
Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][N:9]=2)[S:4][N:3]=1.[NH2:11][CH2:12][CH2:13][CH2:14][NH2:15]>CO>[S:4]1[C:5]2=[N:6][CH:7]=[CH:8][N:9]=[C:10]2[C:2]([NH:11][CH2:12][CH2:13][CH2:14][NH2:15])=[N:3]1

Participants

4

Reactant 2

HCID 4281,3-PropanediamineHCID 569657223-Bromoisothiazolo(4,5-b)pyrazine

Product 1

HCID 58726848N1-(isothiazolo[5,4-b]pyrazin-3-yl)propane-1,3-diamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-bromoisothiazolo[5,4-b]pyrazine in methanol (25 mL) was added 1,3-diaminopropane (6 mL). The reaction mixture was stirred at room temperature for 15 min, then heated to 50° C. After 1 h, the starting material was consumed as judged by LC-MS. The reaction mixture was concentrated under reduced pressure and then partitioned between ethyl acetate and brine. The aqueous layer was back-extracted twice with ethyl acetate and once with methylene chloride. The combined organic layers were washed with brine and dried over anhydrous sodium sulfate and filtered. Concentration under reduced pressure gave N1-(isothiazolo[5,4-b]pyrazin-3-yl)propane-1,3-diamine (410 mg) as a yellow solid. 1H NMR (300 MHz, CDCl3-DMSO-d6): 8.62 (d, 1H), 8.54 (d, 1H), 2.66 (m, 4H), 2.49 (br s, 2H), 1.51 ppm (m, 2H). MW=209 confirmed by LC-MS, tr=2.51 min (Method Y) MH+=208-210.

Workup

  1. temperatureheated to 50° C
  2. waitAfter 1 h
  3. customthe starting material was consumed
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. custompartitioned between ethyl acetate and brine
  6. extractionThe aqueous layer was back-extracted twice with ethyl acetate and once with methylene chloride
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-a5ceeb92051349daa8a7ac2f9d8470a1
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

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