3,4-dihydro-2H-pyran → HCID 178431632, compound

HRID 1269999Notes

Reaction equation

[CH3:1][C:2]1[C:10]([O:11][C@@H:12]2[CH2:17][CH2:16][C@H:15]([N:18]3[C:26](=[O:27])[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19]3=[O:28])[CH2:14][CH2:13]2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[O:29]1[CH:34]=[CH:33][CH2:32][CH2:31][CH2:30]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCCC1>[CH3:1][C:2]1[C:10]([O:11][C@@H:12]2[CH2:17][CH2:16][C@H:15]([N:18]3[C:19](=[O:28])[C:20]4[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:26]3=[O:27])[CH2:14][CH2:13]2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH:30]1[CH2:31][CH2:32][CH2:33][CH2:34][O:29]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 2-{cis-4-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexyl}-1H-isoindole-1,3(2H)-dione (100 mg, 0.266 mmol) in tetrahydrofuran (2.7 ml) were added 3,4-dihydro-2H-pyran (36 μl, 0.399 mmol) and p-toluenesulfonic acid monohydrate (15 mg, 0.069 mmol), and the resulting mixture was stirred for 4 hours while being maintained at 70° C. The reaction solution was allowed to cool, and then was concentrated under reduced pressure to obtain a crude product. The crude product was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 2-{cis-4-[(4-methyl-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-yl)oxy]cyclohexyl}-1H-isoindole-1,3(2H)-dione (99.6 mg, 82%).

Workup

temperatureto cool
concentrationwas concentrated under reduced pressure
customto obtain a crude product
customThe crude product was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record: ord-1b804a0c8c5c4354b969d919cf1c2fb1
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199147B2

Reaction notes

Loading…