Sodium triacetoxyborohydride → 5-{4-[4-(6-fluoro-1H-benzoimidazol-2-yl)-piperidin-1-ylmethyl]-phenyl}-2-methyl-6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidine

Reaction equation

[CH3:1][C:2]1[N:24]=[C:5]2[N:6]=[C:7]([C:16]3[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=3)[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:9][N:4]2[N:3]=1.Cl.[F:26][C:27]1[CH:28]=[CH:29][C:30]2[N:34]=[C:33]([CH:35]3[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]3)[NH:32][C:31]=2[CH:41]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[F:26][C:27]1[CH:28]=[CH:29][C:30]2[N:34]=[C:33]([CH:35]3[CH2:36][CH2:37][N:38]([CH2:20][C:19]4[CH:22]=[CH:23][C:16]([C:7]5[C:8]([C:10]6[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=6)=[CH:9][N:4]6[N:3]=[C:2]([CH3:1])[N:24]=[C:5]6[N:6]=5)=[CH:17][CH:18]=4)[CH2:39][CH2:40]3)[NH:32][C:31]=2[CH:41]=1

Participants

Reactant 3

HCID 5049666Sodium triacetoxyborohydride

HCID 534298905-Fluoro-2-piperidin-4-YL-1H-benzoimidazole hydrochloride

HCID 866306814-(2-Methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

Product 1

HCID 687511975-{4-[4-(6-fluoro-1H-benzoimidazol-2-yl)-piperidin-1-ylmethyl]-phenyl}-2-methyl-6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidine

Procedure

200 mg (0.64 mmol)-4-(2-methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde and 184 mg (0.76 mmol) 6-fluoro-2-piperidine-4-yl-1H-benzimidazole hydrochloride salt were treated as described in example 2.0. Additional NaBH(OAc)3 has been added after 24 and 26 hours (two equivalents each). After stirring at room temperature for five days and the usual workup und purification 142 mg of the desired compound have been obtained.