Benzenamine, 4-(4-morpholinyl)- → HCID 11632995, compound

HRID 729274Notes

Reaction equation

HRID 729274 reaction equation
Cl[C:2]1[C:3](=[O:17])[N:4]([CH2:15][CH3:16])[S:5](=[O:14])(=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[O:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=2)[CH2:20][CH2:19]1>CN(C=O)C>[CH2:15]([N:4]1[C:3](=[O:17])[C:2]([NH:28][C:27]2[CH:26]=[CH:25][C:24]([N:21]3[CH2:22][CH2:23][O:18][CH2:19][CH2:20]3)=[CH:30][CH:29]=2)=[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[S:5]1(=[O:14])=[O:13])[CH3:16]

Participants

4

Reactant 2

HCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 67242996HCID 67242996, compound

Product 1

HCID 11632995HCID 11632995, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-chloro-2-ethyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.217 g, 0.80 mmol) and 4-morpholinoaniline (0.285 g, 1.60 mmol) in DMF (2.0 mL) was heated at 110° C. for 15 mins in a microwave reactor. The mixture was purified by preparative HPLC (C8 50×250, 0.1M NH4OAc/MeCN, gradient) which gave impure product. Repurification was done by preparative HPLC (C8 50×250, 0.1M NMR OAc/MeCN, 50% MeCN isocratic) to give the title compound (0.096 g, 29%) as a solid; 1H NMR (500 MHz, CDCl3): δ 7.22-7.16 (m 1H), 7.12-7.09 (m, 4H), 6.62-6.57 (m 2H), 6.52-6.48 (m, 2H), 3.84 (q, 2H), 3.81-3.78 (m, 4H), 2.99-2.95 (m, 4H), 1.47 (t 3H); 13C NMR (500 MHz, CDCl3): δ 159.4, 149.2, 131.5, 129.5, 128.9, 128.4, 128.1, 125.1, 123.6, 115.6, 109.8, 66.9, 49.7, 35.6, 14.0; Mass Spectrum: M−H+ 414.

Workup

  1. customThe mixture was purified by preparative HPLC (C8 50×250, 0.1M NH4OAc/MeCN, gradient) which
  2. customgave impure product
  3. customRepurification

Sources & evidence

ORD record
ord-aed7cc3bbc0c4381af7b83c6cc80caff
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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