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

HRID 1851273Notes

Reaction equation

HRID 1851273 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.[NH:26]1[CH2:31][CH2:30][CH:29]([C:32]2[NH:36][C:35]3[CH:37]=[C:38]([C:41]([F:44])([F:43])[F:42])[CH:39]=[CH:40][C:34]=3[N:33]=2)[CH2:28][CH2:27]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[CH3:1][C:2]1[N:24]=[C:5]2[N:6]=[C:7]([C:16]3[CH:23]=[CH:22][C:19]([CH2:20][N:26]4[CH2:31][CH2:30][CH:29]([C:32]5[NH:36][C:35]6[CH:37]=[C:38]([C:41]([F:44])([F:43])[F:42])[CH:39]=[CH:40][C:34]=6[N:33]=5)[CH2:28][CH2:27]4)=[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

Participants

4

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 687529342-Piperidine-4-yl-6-trifluoromethyl-1h-benzimidazole hydrochloride saltHCID 866306814-(2-Methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

Product 1

HCID 687514572-methyl-6-phenyl-5-{4-[4-(6-trifluoromethyl-1H-benzimidazol-2-yl)-piperidin-1-ylmethyl]-phenyl}-[1,2,4]-triazolo[1,5-a]pyrimidineYield 30%

Procedure

200 mg (0.64 mmol) 4-(2-methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde and 232 mg (0.64 mmol) 2-piperidine-4-yl-6-trifluoromethyl-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 five days stirring at room temperature the solvents have been evaporated and the residue was purified via chromatography. 109 mg of the desired compound were obtained.

Workup

  1. customhave been evaporated
  2. customthe residue was purified via chromatography

Sources & evidence

ORD record
ord-4b919ca7771940ce955447a9a7c65036
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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