[NH:1]1[CH:5]=[CH:4][C:3]([CH:6]=O)=[N:2]1.[NH2:8][CH2:9][C:10]1[CH:37]=[CH:36][C:13]([CH2:14][N:15]([CH2:26][C:27]2[NH:31][C:30]3[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=3[N:28]=2)[CH:16]2[C:25]3[N:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH2:19][CH2:18][CH2:17]2)=[CH:12][CH:11]=1.[BH4-].[Na+]>CO>[NH:28]1[C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[N:31]=[C:27]1[CH2:26][N:15]([CH2:14][C:13]1[CH:36]=[CH:37][C:10]([CH2:9][NH:8][CH2:6][C:3]2[CH:4]=[CH:5][NH:1][N:2]=2)=[CH:11][CH:12]=1)[CH:16]1[C:25]2[N:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH2:19][CH2:18][CH2:17]1Using General Procedure B: A solution of pyrazol-3-carboxaldehyde (26.6 mg, 0.28 mmol) and (4-aminomethyl-benzyl)-(1H-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (110 mg, 0.28 mmol) in MeOH (2.0 mL) was stirred overnight at room temperature. NaBH4 (21.2 mg, 0.56 mmol) was added and the resultant mixture stirred for an additional 15 minutes. Purification by column chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 100:1:1) afforded the desired amine (80 mg, 60%) as a white foam.
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