Water → (5-(5-(1-phenylcyclopropyl)[1,3]thiazolo[5,4-b]pyridin-2-yl)-1,3-dihydro-2H-isoindol-2-yl)acetic acid

HRID 1177656Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1177656
[C:1]1([C:7]2([C:10]3[N:15]=[C:14]4[S:16][C:17]([C:19]5[CH:20]=[C:21]6[C:25](=[CH:26][CH:27]=5)[CH2:24][N:23]([CH2:28][C:29]([O:31]C)=[O:30])[CH2:22]6)=[N:18][C:13]4=[CH:12][CH:11]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.O.[OH-].[Li+]>C1COCC1>[C:1]1([C:7]2([C:10]3[N:15]=[C:14]4[S:16][C:17]([C:19]5[CH:20]=[C:21]6[C:25](=[CH:26][CH:27]=5)[CH2:24][N:23]([CH2:28][C:29]([OH:31])=[O:30])[CH2:22]6)=[N:18][C:13]4=[CH:12][CH:11]=3)[CH2:8][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67111938Methyl 2-(5-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)isoindolin-2-yl)acetate

Produkt 1

HCID 59174887(5-(5-(1-phenylcyclopropyl)[1,3]thiazolo[5,4-b]pyridin-2-yl)-1,3-dihydro-2H-isoindol-2-yl)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

Methyl 2-(5-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)isoindolin-2-yl)acetate (17 mg, 0.039 mmol) was dissolved in THF (308 μL) and water (77 μL) before lithium hydroxide monohydrate (1 mg, 0.039 mmol) was added and stirred at 65° C. for 2 h. The reaction mixture was concentrated, acidified with 1 N HCl, and filtered. The solid was dissolved in DMSO and eluted through the frit to give the title compound after concentration. MS (ESI) m/z: Calculated: 427.1; Observed: 427.9 (M++H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. filtrationfiltered
  3. dissolutionThe solid was dissolved in DMSO
  4. washeluted through the frit

Quellen und Nachweise

ORD-Eintrag
ord-d21315ec0a144859bd1236724f868973
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842685B2

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