Tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate → HCID 86681955, compound

HRID 1749758Notes

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.[CH:26]([C:28]1[C:36]2[C:31](=[C:32]([CH2:37][N:38]([CH3:46])[C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42])[CH:33]=[CH:34][CH:35]=2)[NH:30][CH:29]=1)=O>CO.N1CCCCC1>[C:41]([O:40][C:39]([N:38]([CH2:37][C:32]1[CH:33]=[CH:34][CH:35]=[C:36]2[C:31]=1[NH:30][CH:29]=[C:28]2/[CH:26]=[C:7]1\[O:8][C:4]2[C:3]([CH2:12][N:13]3[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]3)=[C:2]([OH:1])[CH:11]=[CH:10][C:5]=2[C:6]\1=[O:9])[CH3:46])=[O:45])([CH3:44])([CH3:43])[CH3:42]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.029 g, 0.10 mmol) obtained in Example A16, Step 1 in methanol (3.0 mL) was added with tert-butyl (3-formyl-1H-indole-7-yl)methyl(methyl)carbamate (0.038 g, 0.11 mmol). Then, the mixture was added with 5 drops of piperidine, and the mixture was stirred at 50° C. for 2 hours. The solvent was evaporated under reduced pressure, and then the residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (99:1→95:5)) to obtain tert-butyl (Z)-4-({2-[(7-{[tert-butoxycarbonyl(methyl)amino]methyl}-1H-indol-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.044 g, 71%).

Workup

customThe solvent was evaporated under reduced pressure
washthe residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (99:1→95:5))

Sources & evidence

ORD record: ord-c26bafd484c04fba895524a6100d350b
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156827B2

Reaction notes

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