Piperidine → HCID 178487234, compound

HRID 1749933Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][N:9]=[C:8]2[CH:14]=O)(=[O:4])=[O:3].[CH3:16][O:17][C:18]1[CH:27]=[CH:26][C:21]2[C:22](=[O:25])[CH2:23][O:24][C:20]=2[C:19]=1[CH2:28][N:29]1[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]1.N1CCCCC1>CO>[CH3:16][O:17][C:18]1[CH:27]=[CH:26][C:21]2[C:22](=[O:25])/[C:23](=[CH:14]/[C:8]3[C:7]4[C:11](=[CH:12][CH:13]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=4)[NH:10][N:9]=3)/[O:24][C:20]=2[C:19]=1[CH2:28][N:29]1[CH2:30][CH2:31][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:33][CH2:34]1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 5-(methylsulfonyl)-1H-indazole-3-carboxaldehyde (0.0392 g, 0.175 mmol) in methanol (0.7 mL) was added with tert-butyl 4-[(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.0915 g, 0.252 mmol) synthesized in the same manner as that of Example B42, Step 5, and piperidine (0.00149 g, 0.0175 mmol), and the mixture was stirred at 60° C. for 2 hours. The reaction mixture was concentrated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol) to obtain tert-butyl (Z)-4-[(6-methoxy-2-{[5-(methylsulfonyl)-1H-indazol-3-yl]methylene}-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.0470 g, 47%).

Workup

concentrationThe reaction mixture was concentrated
customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record: ord-645af681236246878c5bba753e736000
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156827B2

Reaction notes

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