Reaction #45490

Reaction equation

4-Amino-3-(3-methoxy-4-{[(1-methyl-1H-indol-2-yl)carbonyl]amino}phenyl)-N-pyrrolidin-3-ylthieno[3,2-c]pyridine-7-carboxamide

acetic acid

carbonate

→

title compound

N-(1-acetylpyrrolidin-3-yl)-4-amino-3-(3-methoxy-4-{[(1-methyl-1H-indol-2-yl)carbonyl]amino}phenyl)thieno[3,2-c]pyridine-7-carboxamide

Conditions

Workup

1. 1
   FiltrationThe mixture was then filtered
2. 2
   Othersolvent removed in vacuo
3. 3
   OtherThe product was purified via flash chromatography

Procedure

4-Amino-3-(3-methoxy-4-{[(1-methyl-1H-indol-2-yl)carbonyl]amino}phenyl)-N-pyrrolidin-3-ylthieno[3,2-c]pyridine-7-carboxamide (100 mg, 0.185 mmol) and acetic acid (9.6 μL, 0.168 mmol) were treated according to General Procedure D. MP-carbonate (184 mg, 0.504 mmol) was added and mixture placed on shaker for 20 hours. The mixture was then filtered and solvent removed in vacuo. The product was purified via flash chromatography to furnish the title compound as a off-white powder. (3.2 mg, 0.0051 mmol): LCMS (Conditions b): MH+=583, Rt=2.85 minutes; 1H NMR (DMSO-d6, 400 MHz) δ 9.50 (1 H), 8.62 (1 H), 8.54 (1 H), 8.00 (1 H), 7.71 (1 H), 7.59 (2 H), 7.35 (2 H), 7.19 (1 H), 7.15 (1 H), 7.06 (1 H), 6.04 (2 H), 4.46-4.56 (1 H), 4.04 (3 H), 3.91 (3 H), 3.80 (1 H), 3.61 (1 H), 3.50 (1 H), 3.39 (1 H), 2.00-2.22 (2 H), 1.96 (3 H).

Source