Potassium Carbonate → HCID 11526582, compound

HRID 899154Notes

Reaction equation

[CH:1]12[O:9][CH:5]([CH2:6][NH:7][CH2:8]1)[CH2:4][N:3]([CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1)[CH2:2]2.[CH3:22][S:23]([N:26]([CH2:34][CH2:35][O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:27][CH2:28]OS(C)(=O)=O)(=[O:25])=[O:24].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:18]([C:17]1[CH:20]=[CH:21][C:14]([O:13][CH2:12][CH2:11][CH2:10][N:3]2[CH2:2][CH:1]3[O:9][CH:5]([CH2:6][N:7]([CH2:28][CH2:27][N:26]([CH2:34][CH2:35][O:36][C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[S:23]([CH3:22])(=[O:25])=[O:24])[CH2:8]3)[CH2:4]2)=[CH:15][CH:16]=1)#[N:19]

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 4-[3-(9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl)-propoxy]-benzonitrile (1.5 g, 5.5 mmol, see WO 01/28992), methanesulfonic acid 2-[methanesulfonyl-(2-phenoxy-ethyl)-amino]-ethyl ester (1.51 g, 4.5 mmol, preparation P above) and dry K2CO3 (1.69 g, 12.3 mmol) in dry acetonitrile (100 ml) was stirred at 60° C. overnight under nitrogen atmosphere. The reaction mixture was filtered and solvent concentrated under reduced pressure. The residue was purified by column chromatography over silica gel using 3% methanol in dichloromethane as eluent to give the title compound (1.4 g) as a liquid.

Workup

filtrationThe reaction mixture was filtered
concentrationsolvent concentrated under reduced pressure
customThe residue was purified by column chromatography over silica gel using 3% methanol in dichloromethane as eluent

Sources & evidence

ORD record: ord-01d0a450471d47fbb22ee7479747a5dd
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07354917B2

Reaction notes

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