Potassium Carbonate → HCID 68521721, compound

HRID 1992358Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of N-(3-Bromo-propyl)-4-cyano-benzenesulfonamide (6.39 g, 0.021 mol; see step (i) above), 9-oxa-3,7-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester (4.32 g, 0.0189 mol see WO 01/28992) and dry K2CO3 (10.16 g, 0.0735 mol) in dry acetonitrile (70 ml) was stirred at 60° C. overnight under N2 atmosphere. The reaction mixture was filtered through celite and filtrate was concentrated under reduced pressure. The residue was purified by column chromatography over silica gel using 50% ethyl acetate in petroleum ether, as eluent to give the sub-title compound (4.29 g) as a solid.

Workup

filtrationThe reaction mixture was filtered through celite and filtrate
concentrationwas concentrated under reduced pressure
customThe residue was purified by column chromatography over silica gel using 50% ethyl acetate in petroleum ether, as eluent

Sources & evidence

ORD record: ord-9e0c696cbbeb4b20a6894455a2225f02
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07648985B2

Reaction notes

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