C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.[CH:21]([NH:24][C:25]1[C:26]2[N:27]([C:37]([O:40][CH3:41])=[N:38][N:39]=2)[C:28]2[C:33]([N:34]=1)=[CH:32][C:31]([CH:35]=O)=[CH:30][CH:29]=2)([CH3:23])[CH3:22].CC(O)=O>ClCCCl>[CH:21]([NH:24][C:25]1[C:26]2[N:27]([C:37]([O:40][CH3:41])=[N:38][N:39]=2)[C:28]2[C:33]([N:34]=1)=[CH:32][C:31]([CH2:35][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[CH:30][CH:29]=2)([CH3:22])[CH3:23]Solid sodium triacetoxyborohydride (59 mg) and morpholine (15 μL) were added to a solution of 4-isopropylamino-1-methoxy-[1,2,4]triazolo[4,3-a]quinoxaline-7-carbaldehyde (50 mg) in 1,2-dichloroethane (1.0 mL). The resulting suspension was stirred at 23° C. for 2.5 hrs., and then a portion of AcOH (10 μL) was added. After an additional 2.5 hrs., the reaction mixture was concentrated. The residue was partitioned between methylene chloride and a saturated aqueous solution of sodium bicarbonate. The organic layer was washed with brine, dried over sodium sulfate and concentrated. Silica gel chromatography afforded isopropyl-(1-methoxy-7-morpholin-4-ylmethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)-amine as a white solid. MS (M+H)+=357.5.
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