Lithium hydroxide, monohydrate → 6-(2-(Benzo[d]isothiazol-3-ylamino)ethylcarbamoyl)nicotinic acid

HRID 502551Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 502551
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([NH:10][CH2:11][CH2:12][NH:13][C:14]([C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][N:17]=2)=[O:15])=[N:2]1.O.[OH-].[Li+]>O1CCCC1.O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([NH:10][CH2:11][CH2:12][NH:13][C:14]([C:16]2[CH:25]=[CH:24][C:19]([C:20]([OH:22])=[O:21])=[CH:18][N:17]=2)=[O:15])=[N:2]1

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 11856360Methyl 6-(2-(benzo[d]isothiazol-3-ylamino)ethylcarbamoyl)nicotinate

Produkt 1

HCID 118563616-(2-(Benzo[d]isothiazol-3-ylamino)ethylcarbamoyl)nicotinic acidAusbeute 63,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl 6-(2(benzo[d]isothiazol-3-ylamino)ethylcarbamoyl)nicotinate (211 mg, 0.6 mmol) was dissolved in a mixture of tetrahydrofuran (5 mL) and water (0.5 mL) and treated with lithium hydroxide monohydrate (100 mg, 2.4 mmol). The reaction mixture was stirred at room temperature overnight. The tetrahydrofuran was removed under vacuum and the residue was diluted with water. Dropwise addition of 50% aqueous hydrochloric acid gave a white solid, which was collected by vacuum filtration and dried to yield 6-(2-(benzo[d]isothiazol-3-ylamino)ethylcarbamoyl)nicotinic acid (130 mg) as a white solid. 1H NMR (300 MHz, CDCl3/DMSO-d6): 9.02 (m, 1H), 8.83 (broad s, 1H), 8.32 (m, 1H), 8.10 (d, 1H), 7.95 (d, 1H), 7.68 (d, 1H), 7.39 (t, 1H), 7.25 (t, 1H), 3.71 ppm (m, 4H). MW=342 confirmed by LC-MS, tr=10.56 min (Method Y) MH+=343

Aufarbeitung

  1. customThe tetrahydrofuran was removed under vacuum
  2. additionthe residue was diluted with water
  3. additionDropwise addition of 50% aqueous hydrochloric acid
  4. customgave a white solid, which
  5. filtrationwas collected by vacuum filtration
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3b63935ff8884981befffea3d040e5c5
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776847B2

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