1-(4-Piperidinyl)-1H-benzimidazole → HCID 86757025, compound

HRID 1068157Notes

Reaction equation

HRID 1068157 reaction equation
[CH:1]([C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)[CH2:6][N:5]([C@H:15]([CH2:26][CH:27]2[CH2:30][CH2:29][CH2:28]2)[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:4]1)=O.[NH:31]1[CH2:36][CH2:35][CH:34]([N:37]2[C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=3[N:39]=[CH:38]2)[CH2:33][CH2:32]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.CN(C=O)C>[N:37]1([CH:34]2[CH2:33][CH2:32][N:31]([CH2:1][C@@H:3]3[C@@H:7]([C:8]4[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=4)[CH2:6][N:5]([C@H:15]([CH2:26][CH:27]4[CH2:28][CH2:29][CH2:30]4)[C:16]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[O:17])[CH2:4]3)[CH2:36][CH2:35]2)[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=2[N:39]=[CH:38]1

Participants

6

Reactant 3

HCID 30192621-(4-Piperidinyl)-1H-benzimidazoleHCID 5049666Sodium triacetoxyborohydrideHCID 54485407HCID 54485407, compound

Product 1

HCID 86757025HCID 86757025, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared from 22 mg of α-(R)-(3-(R)-formyl-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-3-cyclobutylpropionic acid, benzyl ester (prepared above as Aldehyde 2), 27 mg of 1-piperidin-4-yl-1-H-benzoimidazole (from Example 95, Step C) and 40 mg of sodium triacetoxyborohydride in 4 mL of THF and 1 mL of DMF, using a procedure analogous to that described in Example 95, Step D to provide 23 mg of the title compound.

Sources & evidence

ORD record
ord-32f06224a7a649cb964effdd472865b7
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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