[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]1[CH:22]=[C:21]([C:23]2[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])=[C:25]([CH:40]=O)[CH:24]=2)[N:20]=[N:19][C:18]=1[O:42][CH3:43])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN.C(O)(=O)C.[C:50]([BH3-])#[N:51].[Na+]>CO.C1COCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]1[CH:22]=[C:21]([C:23]2[CH:24]=[C:25]([CH2:40][NH:51][CH3:50])[C:26]([O:31][CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:38])([CH3:37])[CH3:39])=[C:27]([O:29][CH3:30])[CH:28]=2)[N:20]=[N:19][C:18]=1[O:42][CH3:43])=[O:7])([CH3:4])([CH3:2])[CH3:3]175 mg of 2-{6-[3-Formyl-5-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-3-methoxy-pyridazin-4-yl}-indole-1-carboxylic acid tert-butyl ester is dissolved in 5 ml of methanol and 0.16 ml of methylamine solution in THF is added. The solution is stirred for 10 min at RT then 19 mg of acetic acid and 20 mg of sodium cyanoborohydride is added. The reaction is stirred for 20 h at RT. The product is purified by preparative RP-HPLC eluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid). Yield 118 mg. LC-MS (ES+) 621 (M+H)+.
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