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

HRID 1851265Notes

Reaction equation

HRID 1851265 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

4

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 534298905-Fluoro-2-piperidin-4-YL-1H-benzoimidazole hydrochlorideHCID 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.

Workup

  1. customthe usual workup und purification 142 mg of the desired compound
  2. customhave been obtained

Sources & evidence

ORD record
ord-a0d8d34f76f24996b85874d2aa01a326
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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