Lithium Hydroxide → 6-(Benzo[d]thiazol-6-ylamino)-4-(isopropylamino)nicotinic acid

HRID 595387Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 595387
[S:1]1[C:5]2[CH:6]=[C:7]([NH:10][C:11]3[CH:21]=[C:20]([NH:22][CH:23]([CH3:25])[CH3:24])[C:14]([C:15]([O:17]CC)=[O:16])=[CH:13][N:12]=3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[Li+].[OH-]>C(O)C.O>[S:1]1[C:5]2[CH:6]=[C:7]([NH:10][C:11]3[CH:21]=[C:20]([NH:22][CH:23]([CH3:25])[CH3:24])[C:14]([C:15]([OH:17])=[O:16])=[CH:13][N:12]=3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 89689730Ethyl 6-(benzo[d]thiazol-6-ylamino)-4-(isopropylamino)nicotinate

Produkt 1

HCID 896896766-(Benzo[d]thiazol-6-ylamino)-4-(isopropylamino)nicotinic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Ethyl 6-(benzo[d]thiazol-6-ylamino)-4-(isopropylamino)nicotinate (3) (1 g, 2.8 mmol) in ethanol (20 mL) and water (5 mL) was stirred at rt then added LiOH (14 mmol, 5 equiv.). The reaction mixture was stirred at room temperature for 4 h, the then heated at 70° C. for 1 h. The solvent was concentrated under reduced pressure, diluted with EtOAc and added water. The aqueous layer was collected and acidified to pH 3-4 using solid citric acid. Solid material precipitated out. Filtered the solid material and dried under vacuum to furnish the title compound (4). LC/MS: Acquity BEH C18 2.1×50 mm, 1.8 micron; Solvent A=0.1% TFA in water; Solvent B=0.1% TFA in ACN; gradient 0-100% B over 2 min; retention time: 0.65 min; LCMS (ES-API), m/z 329.8 (M+H).

Aufarbeitung

  1. temperaturethe then heated at 70° C. for 1 h
  2. concentrationThe solvent was concentrated under reduced pressure
  3. additiondiluted with EtOAc
  4. additionadded water
  5. customThe aqueous layer was collected
  6. customSolid material precipitated out
  7. filtrationFiltered the solid material
  8. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6002128dea2f44e087f22ad984b9c628
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242975B2

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