4-Methylmorpholine → 4'-methoxy-N-(3-(5-(N-(4-methoxybenzyl)sulfamoyl)-benzo[d]isothiazol-3-ylamino)propyl)biphenyl-4-carboxamide

HRID 502577

Reaktionsgleichung

Reaktionsgleichung von HRID 502577
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([OH:17])=O)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(P(=O)(OCC)OCC)#N.CN1CCOCC1.[NH2:35][CH2:36][CH2:37][CH2:38][NH:39][C:40]1[C:44]2[CH:45]=[C:46]([S:49]([NH:52][CH2:53][C:54]3[CH:59]=[CH:58][C:57]([O:60][CH3:61])=[CH:56][CH:55]=3)(=[O:51])=[O:50])[CH:47]=[CH:48][C:43]=2[S:42][N:41]=1>C(Cl)Cl.Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[CH:11][C:12]([C:15]([NH:35][CH2:36][CH2:37][CH2:38][NH:39][C:40]3[C:44]4[CH:45]=[C:46]([S:49](=[O:50])(=[O:51])[NH:52][CH2:53][C:54]5[CH:55]=[CH:56][C:57]([O:60][CH3:61])=[CH:58][CH:59]=5)[CH:47]=[CH:48][C:43]=4[S:42][N:41]=3)=[O:17])=[CH:13][CH:14]=2)=[CH:7][CH:8]=1

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 76257Diethyl cyanophosphonateHCID 27595524'-Methoxy(1,1'-biphenyl)-4-carboxylic acidHCID 587270883-(3-aminopropylamino)-N-(4-methoxybenzyl)benzo[d]isothiazole-5-sulfonamide

Produkt 1

HCID 587269084'-methoxy-N-(3-(5-(N-(4-methoxybenzyl)sulfamoyl)-benzo[d]isothiazol-3-ylamino)propyl)biphenyl-4-carboxamideAusbeute 21,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a solution of 4′-methoxybiphenyl-4-carboxylic acid (34 mg, 0.1 mmol) in methylene chloride (1 mL), diethyl cyanophosphonate (23 μL, 0.2 mmol) and 4-methylmorpholine (34 μL, 0.3 mmol) were added at room temperature and allowed to stir for 15 min. A solution of 3-(3-aminopropylamino)-N-(4-methoxybenzyl)benzo[d]isothiazole-5-sulfonamide (57 mg, 0.1 mmol) in methylene chloride (1 mL) was then added and the resulting reaction mixture was allowed to stir for 7 h. Upon diluting the reaction mixture with methylene chloride (20 mL) and 10% HCl aqueous solution, a precipitate was observed, filtered and air-dried to provide 4′-methoxy-N-(3-(5-(N-(4-methoxybenzyl)sulfamoyl)-benzo[d]isothiazol-3-ylamino)propyl)biphenyl-4-carboxamide (13 mg). 1H NMR (300 MHz, DMSO-d6): 9.01 (br s, 1H), 8.58 (t, 1H), 8.47 (d, 1H), 7.88-7.91 (m, 3H), 7.70 (d, 2H), 7.66 (d, 2H), 7.50 (dd, 1H), 7.34 (d, 1H), 7.13 (d, 2H), 7.03 (d, 2H), 6.78 (d, 2H), 3.88 (d, 2H), 3.80 (s, 3H), 3.67 (s, 3H), 3.42-3.48 (m, 2H), 3.31 (m, 2H), 2.00-2.09 ppm (m, 2H). MW=616 confirmed by LC-MS, tr=13.65 min (Method Y) MH+=617.

Aufarbeitung

  1. customthe resulting reaction mixture
  2. stirringto stir for 7 h
  3. filtrationfiltered
  4. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-dbe374103b454f5f82e27f307816c0d1
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776847B2

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