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

HRID 502576

反応式

HRID 502576 の反応式
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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cb89a25e5c09423a9782fd3c2a17ed53
出典データセット
uspto-grants-2010_08
特許番号
US07776847B2

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