Sodium triacetoxyborohydride → 2-{1-[4-(2-methyl-6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzyl]-piperidin-4-yl}-3H-benzimidazole-5-carbonitrile

HRID 1851272Notes

Reaction equation

HRID 1851272 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:33][C:34]3[CH:40]=[C:39]([C:41]#[N:42])[CH:38]=[CH:37][C:35]=3[N:36]=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[CH2:27][CH2:28][CH:29]([C:32]5[NH:33][C:34]6[CH:40]=[C:39]([C:41]#[N:42])[CH:38]=[CH:37][C:35]=6[N:36]=5)[CH2:30][CH2:31]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 687529322-Piperidin-4-yl-1h-benzoimidazole-5-carbonitrile hydrochloride saltHCID 866306814-(2-Methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

Product 1

HCID 687509072-{1-[4-(2-methyl-6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzyl]-piperidin-4-yl}-3H-benzimidazole-5-carbonitrileYield 36%

Procedure

200 mg (0.64 mmol) 4-(2-methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde and 200 mg (0.64 mmol) 2-piperidine-4-yl-3H-benzimidazole-5-carbonitrile 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. 121 mg of the desired compound were obtained.

Workup

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

Sources & evidence

ORD record
ord-fe54f2e972ba4bc2baa2b8ba578f5b38
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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