Piperidine → HCID 86682032, compound

HRID 1749899Notes

Reaction equation

[CH3:1][Si:2]([CH3:19])([CH3:18])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH:16]=O)=[N:8]1.[OH:20][C:21]1[CH:30]=[CH:29][C:24]2[C:25](=[O:28])[CH2:26][O:27][C:23]=2[C:22]=1[CH2:31][N:32]1[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]1.N1CCCCC1>CO>[OH:20][C:21]1[CH:30]=[CH:29][C:24]2[C:25](=[O:28])/[C:26](=[CH:16]/[C:9]3[C:10]4[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=4)[N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:19])([CH3:18])[CH3:1])[N:8]=3)/[O:27][C:23]=2[C:22]=1[CH2:31][N:32]1[CH2:33][CH2:34][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:36][CH2:37]1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of the positional isomer (2) of N-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole-3-carboxaldehyde (0.354 g, 1.28 mmol) obtained in Step 1 in methanol (5 mL) was added with tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.446 g, 1.28 mmol) and piperidine (0.0109 g, 0.128 mmol), and the mixture was stirred at 60° C. for 5 hours. The reaction mixture was concentrated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain tert-butyl (Z)-4-({6-hydroxy-3-oxo-2-[(N-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazol-3-yl)methylene]-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.419 g, 53%).

Workup

concentrationThe reaction mixture was concentrated
customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-aa07ab338983418b8a0b19d77a39689f
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156827B2

Reaction notes

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