Piperidine → HCID 178493636, compound

HRID 1750009Notes

Reaction equation

[F:1][C:2]1[C:3]([O:27][CH3:28])=[C:4]([CH2:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[C:5]2[O:9][CH2:8][C:7](=[O:10])[C:6]=2[CH:11]=1.[NH:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([CH:38]=O)=[N:30]1.N1CCCCC1>CO>[NH:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31](/[CH:38]=[C:8]2\[O:9][C:5]3[C:4]([CH2:12][CH2:13][CH:14]4[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:18][CH2:19]4)=[C:3]([O:27][CH3:28])[C:2]([F:1])=[CH:11][C:6]=3[C:7]\2=[O:10])=[N:30]1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of tert-butyl 4-[2-(5-fluoro-6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)ethyl]piperidine-1-carboxylate (0.0245 g, 0.0623 mmol) in methanol (3 mL) was added with 1H-indazole-3-carboxaldehyde (0.0100 g, 0.0685 mmol) and piperidine (0.100 mL, 1.01 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-(2{-2-[(1H-indazol-3-yl)methylene]-5-fluoro-6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl}ethyl)piperidine-1-carboxylate (0.0231 g, 71%).

Workup

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

Sources & evidence

ORD record: ord-8c370fe4b01e48389551d424d61134da
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156827B2

Reaction notes

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