Pyridine → (1S,4S)-2-Oxa-5-aza-bicyclo[2.2.1]heptane-5-carboxylic Acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide

HRID 2086553Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2086553
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH2:12])[S:11][C:7]=2[C:6]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:5][CH:4]=1.N1C=CC=CC=1.Cl[C:26](OC1C=CC=CC=1)=[O:27].[C@H:35]12[CH2:41][C@H:38]([NH:39][CH2:40]1)[CH2:37][O:36]2.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH:12][C:26]([N:39]3[CH2:40][C@@H:35]4[CH2:41][C@H:38]3[CH2:37][O:36]4)=[O:27])[S:11][C:7]=2[C:6]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:5][CH:4]=1

Komponenten

7

Edukt 5

HCID 1049PyridineHCID 10340Sodium CarbonateHCID 15891Phenyl chloroformateHCID 11159293(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptane hydrobromideHCID 114028614-Methoxy-7-morpholinobenzo[d]thiazol-2-amine

Produkt 1

HCID 11188451(1S,4S)-2-Oxa-5-aza-bicyclo[2.2.1]heptane-5-carboxylic Acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amideAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine (265 mg, 1.0 mmol) in dichloromethane (15 ml) is subsequently added pyridine (0.24 ml, 3.0 mmol) and phenyl chloroformate (0.15 ml, 1.2 mmol) and the resulting solution stirred for 45 min at ambient temperature. Then (1S,4S)-2-oxa-5-aza-bicyclo[2.2.1]heptane (490 mg, 3.6 mmol) is added and the mixture stirred at ambient temperature for 15 min and at 40° C. for 2.5 h. After cooling to ambient temperature, saturated aqueous sodium carbonate (15 ml) is added, the organic phase is separated, dryed and the solvent evaporated in vacuo. Flash chromatography (silica, eluent: dichloromethane containing methanol (gradient from 0 to 5%)) afforded the title compound as white crystals (135 mg, 35% yield). MS: m/e=391(M+H+).

Aufarbeitung

  1. stirringthe mixture stirred at ambient temperature for 15 min and at 40° C. for 2.5 h
  2. temperatureAfter cooling to ambient temperature
  3. customthe organic phase is separated
  4. customthe solvent evaporated in vacuo
  5. additionFlash chromatography (silica, eluent: dichloromethane containing methanol (gradient from 0 to 5%))

Quellen und Nachweise

ORD-Eintrag
ord-ee4ad22c446b4260a58d6d2affbb1067
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06727247B2

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