Water → Ethyl cis(+/-)-2-(3-amino-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-benzothiazole-7-carboxylate

HRID 1425015

Reaktionsgleichung

Reaktionsgleichung von HRID 1425015
[N:1]([C@H:4]1[C@@H:9]([NH:10][C:11]([C:13]2[NH:14][C:15]([CH2:19][CH3:20])=[C:16]([Cl:18])[N:17]=2)=[O:12])[CH2:8][CH2:7][N:6]([C:21]2[S:22][C:23]3[C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:28][CH:27]=[CH:26][C:24]=3[N:25]=2)[CH2:5]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[NH2:1][C@H:4]1[C@@H:9]([NH:10][C:11]([C:13]2[NH:14][C:15]([CH2:19][CH3:20])=[C:16]([Cl:18])[N:17]=2)=[O:12])[CH2:8][CH2:7][N:6]([C:21]2[S:22][C:23]3[C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:28][CH:27]=[CH:26][C:24]=3[N:25]=2)[CH2:5]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86648559Ethyl cis(+/-)-2-(3-azido-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-benzothiazole-7-carboxylate

Produkt 1

HCID 86648558Ethyl cis(+/-)-2-(3-amino-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-benzothiazole-7-carboxylateAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Ethyl cis(±)-2-(3-azido-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-benzothiazole-7-carboxylate obtained in Example (81d) (84 mg, 0.17 mmol) was dissolved in THF (3 mL). Triphenylphosphine (63 mg, 0.24 mmol) and distilled water (0.2 mL) were added, and the mixture was heated under reflux for 15 hours. The reaction solution was concentrated under reduced pressure and the precipitated solid was collected by filtration, to obtain 59.6 mg of the title compound as a white solid (75%).

Aufarbeitung

  1. additionwere added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 15 hours
  4. concentrationThe reaction solution was concentrated under reduced pressure
  5. filtrationthe precipitated solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-ed44a5f0d42a4b6b932def69786925ea
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927588B2

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