[CH3:1][C:2]1([CH3:21])[CH2:8][CH2:7][CH2:6][N:5]([C:9]([C:11]2[CH:15]=[C:14]([C:16]3[CH:17]=[N:18][NH:19][CH:20]=3)[S:13][CH:12]=2)=[O:10])[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][CH2:30][OH:31]>CN(C=O)C>[CH3:1][C:2]1([CH3:21])[CH2:8][CH2:7][CH2:6][N:5]([C:9]([C:11]2[CH:15]=[C:14]([C:16]3[CH:17]=[N:18][N:19]([CH2:29][CH2:30][OH:31])[CH:20]=3)[S:13][CH:12]=2)=[O:10])[CH2:4][CH2:3]1(4,4-Dimethyl-azepan-1-yl)-[5-(1H-pyrazol-4-yl)-thiophen-3-yl]-methanone (0.075 g, 0.25 mmol) was dissolved in DMF (1 mL) and potassium carbonate (44 mg, 0.32 mmol) was added followed by 2-bromoethanol (27 μL, 0.38 mmol). The reaction mixture was heated at 100° C. overnight then quenched by addition of ammonium chloride. The mixture was extracted with ethyl acetate (×2) then the organics were washed with lithium chloride (15% aqueous solution) and evaporated. The crude material was purified by chromatography on a silica II cartridge, eluting with 10-66% ethyl acetate in cyclohexane. The residue was purified by HPLC, eluting with 10%-98% acetonitrile in water (0.1% formic acid) over 20 minutes. The fractions containing the desired product were concentrated under vacuum and freeze-dried to give the title compound as a colourless oil (0.020 g). LCMS m/z 348.29 [M+H]+ R.T.=8.62 min (Analytical Method 2).
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