Reaktion #73379

Reaktionsgleichung

5-(6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yloxy)-N-(3-(trifluoromethyl)phenyl)-1H-indole-1-carboxamide

2-bromoacetamide

→

5-(6-carbamoylmethyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yloxy)-indole-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction is concentrated
2. 2
   Sonstigethe residue absorbed onto silica gel
3. 3
   Sonstigeseparated via FCC (0-10%, 10% NH4 in MeOH:DCM)

Vorschrift

5-(6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yloxy)-N-(3-(trifluoromethyl)phenyl)-1H-indole-1-carboxamide (217 mg, 0.494 mmol) is dissolved in DMF (5 mL) and TEA (160 μl, 1.15 mmol) is added followed by 2-bromoacetamide (250 mg, 1.81 mmol). The solution is stirred at it for 1 h. The reaction is concentrated and the residue absorbed onto silica gel and separated via FCC (0-10%, 10% NH4 in MeOH:DCM) to obtain 5-(6-carbamoylmethyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yloxy)-indole-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide. MS (ESI) m/z 497.9 (M+1); 1H NMR (400 MHz, MeOD) δ ppm 10.38 (br. S., 1 H)8.58 (s, 1 H)8.27 (d, J=8.84 Hz, 1 H)8.09-8.13 (m, 2 H)7.96 (s, 1 H)7.65 (t, J=8.08 Hz, 1 H)7.48-7.51 (m, 2 H)7.38 (br. S., 1 H)7.09-7.17 (m, 2 H) 6.80 (d, J=3.03 Hz, 1 H)4.12 (dd, J=10.61, 2.02 Hz, 4H)3.38 (s, 2 H).

Quelle