1,3-Propanediamine → 3-(3-aminopropylamino)-N-(4-methoxybenzyl)benzo[d]isothiazole-5-sulfonamide

HRID 502576Notes

Reaction equation

HRID 502576 reaction equation
Cl[C:2]1[C:6]2[CH:7]=[C:8]([S:11]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)(=[O:13])=[O:12])[CH:9]=[CH:10][C:5]=2[S:4][N:3]=1.O.[NH2:25][CH2:26][CH2:27][CH2:28][NH2:29]>>[NH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:2]1[C:6]2[CH:7]=[C:8]([S:11]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)(=[O:13])=[O:12])[CH:9]=[CH:10][C:5]=2[S:4][N:3]=1

Participants

4

Reactant 3

HCID 4281,3-PropanediamineHCID 962WaterHCID 587270493-chloro-N-(4-methoxybenzyl)benzo[d]isothiazole-5-sulfonamide

Product 1

HCID 587270883-(3-aminopropylamino)-N-(4-methoxybenzyl)benzo[d]isothiazole-5-sulfonamide

Procedure

A solution of 3-chloro-N-(4-methoxybenzyl)benzo[d]isothiazole-5-sulfonamide (52 mg, 0.1 mmol) in 1,3-diaminopropane (1 mL) was allowed to stir at room temperature for 80 min. The dark brown reaction mixture was then poured over water (10 mL) and extracted with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 3-(3-aminopropylamino)-N-(4-methoxybenzyl)benzo[d]isothiazole-5-sulfonamide (57 mg) as an orange oil. 1H NMR (300 MHz, CD3OD): 8.22 (dd,1H), 7.54 (dd, 1H), 7.29 (dd, 1H), 7.04 (d, 2H), 6.64 (d, 2H), 4.00 (s, 2H), 3.64 (s, 3H), 3.36 (t, 2H), 2.82 (d, 2H), 1.94-2.02 ppm (m, 2H). MW=406 confirmed by LC-MS, tr=7.95 min (Method Y) MH+=407.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cb89a25e5c09423a9782fd3c2a17ed53
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

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