Reaktion #67938

Reaktionsgleichung

Compound 8

2-(4-tert-Butoxycarbonylamino-1-methyl-1H-pyrrole-2-yl)-3H-imidazo[4,5-b]pyridine-5-carboxylic Acid Methyl Ester

HCl

→

9

Ausbeute 81.0%

2-(4-tert-Butoxycarbonylamino-1-methyl-1H-pyrrole-2-yl)-3H-imidazo[4,5-b]pyridine-5-carboxylic acid

Ausbeute 81.0%

Lösungsmittel

NaOH

H2O dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe solution was cooled to 0° C.
2. 2
   SonstigeThe product was separated by centrifugation
3. 3
   Sonstigethe supernatant removed
4. 4
   Waschenthe formed precipitate washed with cold H2O (2×2 mL)

Vorschrift

Compound 8 (60 mg, 0.6 mmol) was dissolved in 0.2 M NaOH in H2O/dioxane 1:1 (7 mL) and stirred for 5 h at r.t. while the solution turned orange. The solution was cooled to 0° C. and 1N HCl was added dropwise until pH 1-2, while an orange precipitate developed. The product was separated by centrifugation, the supernatant removed, and the formed precipitate washed with cold H2O (2×2 mL). Lyophilization afforded 46 mg (81%) of 9 as an orange solid. Data of 9: UV (MeOH): λmax 359. 1H NMR (300 MHz, DMSO-d6): δ 1.46 (s, 9H), 4.05 (s, 3H), 7.01 (brs, 1H, D2O exchange), 7.15 (s, 1H), 7.98 (m, 3H), 9.30 (s, 1H, D2O exchange). 13C NMR (75 MHz, DMSO-d6): δ 28.96, 37.47, 79.21, 106.38, 118.65, 119.93, 120.44, 122.32, 124.99, 141.58, 150.32, 153.38, 166.53. MS (ESI): m/z (rel intensity) 358 (100). HRMS (FAB): m/z calcd for C17H20N5O4, 358.1515; found, 358.1506.

Quelle