[CH2:1]([N:8]1[C:17]2[C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[N:14]([C:22]([C:24]3[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[C:26]([CH3:32])[CH:25]=3)=[O:23])[CH2:13][CH2:12][C:11]=2[N:10]=[C:9]1[CH3:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].N>CO.O.O.O.O.O.O.[Co](Cl)Cl>[NH2:29][CH2:28][C:27]1[CH:30]=[CH:31][C:24]([C:22]([N:14]2[CH2:13][CH2:12][C:11]3[N:10]=[C:9]([CH3:33])[N:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[C:17]=3[C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]2=3)=[O:23])=[CH:25][C:26]=1[CH3:32]A solution of 4-(1-benzyl-2-methyl-4,5-dihydro-1H-1,3,6-triaza-benzo[e]azulene-6-carbonyl)-2-methyl-benzonitrile from Example E121.1 (830 mg, 1.9 mmol) in methanol (10 ml) at room temperature was treated with cobalt(II) chloride hexahydrate (913 mg, 3.8 mmol). The mixture was stirred for 15 min then cooled down to 0° C. Sodium borohydride (726 mg, 19 mmol) was added portion-wise and the reaction mixture was stirred for 2 h at room temperature. 35% Ammonia (5 ml) was added dropwise and the mixture was stirred for 30 min then concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 1% 35% ammonia:9% methanol:90% dichloromethane) to yield the title compound (680 mg, 81%).
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