N(C(OC(C)C)=O)=NC(OC(C)C)=O.[OH:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23].[Br:27][C:28]1[N:29]=[CH:30][C:31]([NH:34][C:35]2[CH:39]=[C:38]([C:40]3[C:45]([O:46][CH3:47])=[CH:44][CH:43]=[CH:42][C:41]=3O)[NH:37][N:36]=2)=[N:32][CH:33]=1>C1COCC1>[Br:27][C:28]1[N:29]=[CH:30][C:31]([NH:34][C:35]2[CH:39]=[C:38]([C:40]3[C:45]([O:46][CH3:47])=[CH:44][CH:43]=[CH:42][C:41]=3[O:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24])[NH:37][N:36]=2)=[N:32][CH:33]=1Diisopropyl azodicarboxylate (1.73 mL, 8.76 mmol) is added to a stirred solution of tert-butyl 3-hydroxypropylcarbamate (0.83 mL, 4.83 mmol), 2-(3-(5-bromopyrazin-2-ylamino)-1H-pyrazol-5-yl)-3-methoxyphenol) (1.59 g, 4.38 mmol) and polystyrene triphenylphosphine (5.91 g, 8.76 mmol) in THF (50 mL) at room temperature. After stirring for 45 min, the reaction is filtered, and the solvent is removed under reduced pressure. The resulting residue is chromatographed (methanol/CH2Cl2) to afford 1.27 g (54%) of a yellow solid.
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