CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:25][C:26]1[S:27][C:28]2[CH:34]=[CH:33][C:32]([C:35]([OH:37])=O)=[CH:31][C:29]=2[N:30]=1.[Si:38]([O:45][CH2:46][CH2:47][C:48]1[CH:49]=[C:50]([CH2:53][N:54]2[CH2:64][CH2:63][C:57]3([O:62][CH2:61][CH2:60][NH:59][CH2:58]3)[CH2:56][CH2:55]2)[S:51][CH:52]=1)([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39].C(N(CC)CC)C>CN(C=O)C>[CH3:28][CH2:29][CH2:31][CH:32]([CH3:35])[CH3:33].[Si:38]([O:45][CH2:46][CH2:47][C:48]1[CH:49]=[C:50]([CH2:53][N:54]2[CH2:64][CH2:63][C:57]3([O:62][CH2:61][CH2:60][N:59]([C:35]([C:32]4[CH:33]=[CH:34][C:28]5[S:27][C:26]([CH3:25])=[N:30][C:29]=5[CH:31]=4)=[O:37])[CH2:58]3)[CH2:56][CH2:55]2)[S:51][CH:52]=1)([C:41]([CH3:42])([CH3:43])[CH3:44])([CH3:40])[CH3:39]HATU (0.333 g) was added to stirred solution of 2-methylbenzo[d]thiazole-5-carboxylic acid (0.17 g), 9-((4-(2-(tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecane (example 43, step b) (0.3 g) and triethylamine (0.407 mL) in DMF (3 mL). After 1 h, the reaction mixture was partitioned between water and ethyl acetate. The ethyl acetate layer was washed twice with water, once with brine, dried over magnesium sulphate, filtered and evaporated in vacuo. Purification by silica gel chromatography eluting with ethyl acetate:isohexane:triethylamine, 2:8:1 gave the subtitled compound as a gum. Yield 0.36 g.
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