Piperidine → HCID 49833164, compound

HRID 1947525Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH2:20][CH2:21]OS(C)(=O)=O.[NH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>CC#N>[N:27]1([CH2:21][CH2:20][C:14]2[C:13]3[C:17](=[CH:18][CH:19]=[C:11]([O:10][C:2]4[S:1][C:5]5[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=5[N:3]=4)[CH:12]=3)[NH:16][CH:15]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methanesulfonic acid 2-[5-(benzothiazol-2-yloxy)-1H-indol-3-yl]-ethyl ester (100 mg, 0.26 mmol) in MeCN (3 mL) was added piperidine (0.03 mL, 0.31 mmol) and the reaction mixture was heated (80° C., 2 h). The reaction mixture was cooled (rt), filtered and purified by basic reverse phase HPLC to provide the title compound as a white solid (47.2 mg, 49%). MS (ESI): mass calcd. for C22H23N3OS, 377.5; m/z found, 378.3 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.08 (s, 1H), 7.77 (d, J=7.6, 1H), 7.65 (d, J=8.0, 1H), 7.59 (d, J=2.3, 1H), 7.43-7.36 (m, 2H), 7.26 (s, 1H), 7.18 (dd, J=8.7, 2.3, 1H), 7.14 (s, 1H), 3.02-2.90 (m, 2H), 2.71-2.63 (m, 2H), 2.51 (s, 4H), 1.63 (dd, J=11.3, 5.6, 4H), 1.47 (s, 2H).

Workup

temperatureThe reaction mixture was cooled (rt)
filtrationfiltered
custompurified by basic reverse phase HPLC

Sources & evidence

ORD record: ord-d094d8c3b39e4e92988c6bfc2ce0156b
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399465B2

Reaction notes

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