Potassium Carbonate → 1,1-Dimethylethyl N-[3-[7-[2-(4-cyano-2-fluorophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl]propyl]carbamate

HRID 1992368Notes

Reaction equation

Cl.Cl.[F:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH2:14][N:15]1[CH2:22][CH:21]2[O:23][CH:17]([CH2:18][NH:19][CH2:20]2)[CH2:16]1)[C:7]#[N:8].[C:24]([O:28][C:29](=[O:35])[NH:30][CH2:31][CH2:32][CH2:33]Br)([CH3:27])([CH3:26])[CH3:25].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:24]([O:28][C:29](=[O:35])[NH:30][CH2:31][CH2:32][CH2:33][N:19]1[CH2:20][CH:21]2[O:23][CH:17]([CH2:16][N:15]([CH2:14][CH2:13][O:12][C:11]3[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=3[F:3])[CH2:22]2)[CH2:18]1)([CH3:27])([CH3:26])[CH3:25]

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 3-Fluoro-4-[2-(9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl)-ethoxy]-benzonitrile hydrochloride hydrochloric acid salt (5 g, 0.0137 mol, from step N (vii) above ), (3-Bromo-propyl)-carbamic acid tert-butyl ester (4.24 g, 0.0178 mol, from step (i) above) and potassium carbonate (7.57 g, 0.0548 mol) in dry acetonitrile (100 ml) was stirred at 60° C. overnight under nitrogen atmosphere. The reaction mixture was filtered through celite and solvent concentrated under reduced pressure. The residue was purified by column chromatography over silica gel using 5% methanol in dichloromethane as eluent to give the sub-title compound (5.8 g) as yellow oil.

Workup

filtrationThe reaction mixture was filtered through celite and solvent
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography over silica gel using 5% methanol in dichloromethane as eluent

Sources & evidence

ORD record: ord-677797d172414f9c92824a282affa782
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07648985B2

Reaction notes

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