Piperidine → HCID 178488166, compound

HRID 1749873Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of tert-butyl 4-[1-(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.313 g, 0.898 mmol) in methanol (4 mL) was added with 5-methoxy-1H-indazole-3-carbaldehyde (0.158 g, 0.898 mmol), and piperidine (0.00764 g, 0.0898 mmol) at room temperature, and the mixture was stirred at 60° C. for 2 hours. The reaction mixture was concentrated, and the resulting residue was suspended in acetonitrile and thereby washed to obtain tert-butyl (Z)-4-({6-hydroxy-3-oxo-2-[(5-methoxy-1H-indazol-3-yl)methylene]-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.318 g, 69%).

Workup

concentrationThe reaction mixture was concentrated
washwashed

Sources & evidence

ORD record: ord-11dfbfd466a0459faf7e52cf85ebbe0b
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156827B2

Reaction notes

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