Potassium Carbonate → 1-{2-[5-(6,7-Dihydro-5H-1,4,8a-triaza-s-indacen-8-yl)-benzofuran-2-yl]-ethyl}-pyrrol idin-3-(S)-ol

HRID 2251127Notes

Reaction equation

[N:1]1[N:12]2[C:4]([N:5]=[C:6]3[C:10](=[C:11]2[C:13]2[CH:14]=[CH:15][C:16]4[O:20][C:19]([CH2:21][CH2:22]OS(C)(=O)=O)=[CH:18][C:17]=4[CH:28]=2)[CH2:9][CH2:8][CH2:7]3)=[CH:3][CH:2]=1.[OH:29][C@H:30]1[CH2:34][CH2:33][NH:32][CH2:31]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:1]1[N:12]2[C:4]([N:5]=[C:6]3[C:10](=[C:11]2[C:13]2[CH:14]=[CH:15][C:16]4[O:20][C:19]([CH2:21][CH2:22][N:32]5[CH2:33][CH2:34][C@H:30]([OH:29])[CH2:31]5)=[CH:18][C:17]=4[CH:28]=2)[CH2:9][CH2:8][CH2:7]3)=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Methanesulfonic acid 2-[5-(6,7-dihydro-5H-1,4,8a-triaza-s-indacen-8-yl)-benzo-furan-2-yl]-ethyl ester (0.085 mmol) described above was dissolved in acetonitrile (2 ml) followed by addition of 3-(S)-hydroxypyrrolidine (0.85 mmol) and potassium carbonate (0.425 mmol) and heated to 70° C. for 24 hours. The reaction was cooled, filtered and concentrated. The residue was purified via preparative HPLC to give 1-{2-[5-(6,7-Dihydro-5H-1,4,8a-triaza-s-indacen-8-yl)-benzofuran-2-yl]-ethyl}-pyrrol idin-3-(S)-ol.

Workup

temperatureThe reaction was cooled
filtrationfiltered
concentrationconcentrated
customThe residue was purified via preparative HPLC

Sources & evidence

ORD record: ord-9b4d310a12314795a82298e898f35810
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07319103B2

Reaction notes

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