Potassium Carbonate → HCID 15980221, compound

HRID 1992356Notes

Reaction equation

[CH:1]12[O:9][CH:5]([CH2:6][NH:7][CH2:8]1)[CH2:4][N:3]([CH2:10][CH2:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1)[CH2:2]2.[C:21]([O:25][C:26](=[O:32])[NH:27][CH2:28][CH2:29][CH2:30]Br)([CH3:24])([CH3:23])[CH3:22].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:21]([O:25][C:26](=[O:32])[NH:27][CH2:28][CH2:29][CH2:30][N:7]1[CH2:8][CH:1]2[O:9][CH:5]([CH2:4][N:3]([CH2:10][CH2:11][O:12][C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=3)[CH2:2]2)[CH2:6]1)([CH3:24])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 4-[2-(9-Oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl)-ethoxy]-benzonitrile (6.5 g, 0.02 mol, see WO 01/28992), (3-Bromo-propyl)-carbamic acid tert-butyl ester (6.0 g, 0.025 mol) and dry K2CO3 (13.08 g, 0.0946 mol) in 40 ml of dry acetonitrile was stirred at 60° C. overnight under N2 atmosphere. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography over silica gel using 20% ethyl acetate in petroleum ether as eluent to yield sub-title compound (3.5 g) as a liquid.

Workup

filtrationThe reaction mixture was filtered through celite
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by column chromatography over silica gel using 20% ethyl acetate in petroleum ether as eluent

Sources & evidence

ORD record: ord-04307261973840b6a9c480d18726f0b4
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07648985B2

Reaction notes

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