Potassium Carbonate → HCID 57662043, compound

HRID 1665316Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][C:4]2([O:11][C:10]3[C:12]4[C:17]([C:18](=[O:21])[C:19](=[O:20])[C:9]=3[S:8][CH2:7]2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH2:3][CH2:2]1.Br[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:31]=[N:32][NH:33][CH:34]=2)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[NH:32]1[CH:31]=[C:30]([C:27]2[CH:28]=[CH:29][C:24]([CH2:23][N:1]3[CH2:2][CH2:3][C:4]4([O:11][C:10]5[C:12]6[C:17]([C:18](=[O:21])[C:19](=[O:20])[C:9]=5[S:8][CH2:7]4)=[CH:16][CH:15]=[CH:14][CH:13]=6)[CH2:5][CH2:6]3)=[CH:25][CH:26]=2)[CH:34]=[N:33]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of spiro[naphtho[1,2-b][1,4]oxathiine-2,4′-piperidine]-5,6-dione (0.15 g, 0.5 mmol) in anhydrous acetonitrile (5.0 mL) was added 4-[4-(bromomethyl)phenyl]-1H-pyrazole (0.24 g, 1.0 mmol) followed by potassium carbonate (0.20 g, 1.5 mmol). The reaction mixture was stirred at 70° C. for 16 h. The reaction mixture was filtered to remove all the solids and the solvent removed under vacuum. The crude product was purified by reverse phase HPLC to give the desired product as a purple solid (0.005 g, 2.3%). M.p.=190-192° C.; 400 MHz 1H NMR (CDCl3) δ: 8.1 (d, 1H), 7.9 (s, 1H), 7.8 (d, 1H), 7.6-7.7 (m, 4H), 7.5 (t, 1H), 7.4 (d, 2H), 6.5 (s, 1H), 3.6 (s, 2 h), 2.9 (s, 2 h), 2.8 (d, 2H), 2.5 (t, 2H), 2.1 (d, 2H), 1.9 (t, 2H); LCMS: 458 [M+H].

Workup

filtrationThe reaction mixture was filtered
customto remove all the solids
customthe solvent removed under vacuum
customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-a59e1c2f35c2400f8ea0a5763328382d
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039503B2

Reaction notes

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