Diisopropyl Ether → HCID 118071679, compound

HRID 1775456Notes

Reaction equation

Cl.[NH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[NH:7][C:6]=1[C:16]([NH:18][CH3:19])=[O:17].C([N:23]([CH:26](C)C)CC)(C)C.[OH-:29].[Na+].C([O:34][CH:35](C)C)(C)C>C(Cl)(Cl)Cl.O1CCCC1>[CH3:15][O:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:16]([NH:18][CH3:19])=[O:17])=[C:5]2[CH2:4][CH2:3][NH:2][C:26](=[O:29])[NH:23][O:34][CH3:35]

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 3-(2-aminoethyl)-5-methoxy-N-methyl-1H-indole-2-carboxamide hydrochloride (116 mg), diisopropylethylamine (0.146 mL), and tetrahydrofuran (4.63 mL) was added 4-nitrophenyl 1-methoxycarbamate (90.9 mg), warming to 60° C. and stirring for 3.5 hours. To the mixture were added chloroform and a 1 M aqueous sodium hydroxide solution, followed by stirring, and the organic layer was separated using a phase separator (Biotage) and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=50:1 to 10:1 amino silica gel). The obtained crude product was solidified with diisopropyl ether, and the obtained solid was collected by filtration and dried under reduced pressure to obtain 5-methoxy-3-{2-[(methoxycarbamoyl)amino]ethyl}-N-methyl-1H-indole-2-carboxamide (42.6 mg).

Workup

stirringby stirring
customthe organic layer was separated
concentrationconcentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=50:1 to 10:1 amino silica gel)
customThe obtained crude product
filtrationthe obtained solid was collected by filtration
customdried under reduced pressure

Sources & evidence

ORD record: ord-20fde61635d44771a4d96ea41578b51d
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260445B2

Reaction notes

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