[4-(Piperazin-1-yl)phenyl]boronic acid → N-(cyanomethyl)-4-methyl-2-[(4'-piperazin-1-yl-1,1'-biphenyl-4-yl)(pyridin-2-yl)methoxy]pentanamide

HRID 1180401Notes

Reaction equation

HRID 1180401 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[O:9][CH:10]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:11]([NH:13][CH2:14][C:15]#[N:16])=[O:12])=[CH:4][CH:3]=1.[N:27]1([C:33]2[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=2)[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>>[C:15]([CH2:14][NH:13][C:11](=[O:12])[CH:10]([O:9][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([C:36]2[CH:35]=[CH:34][C:33]([N:27]3[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]3)=[CH:38][CH:37]=2)=[CH:3][CH:4]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)[CH2:17][CH:18]([CH3:20])[CH3:19])#[N:16]

Participants

3

Reactant 2

HCID 5233013[4-(Piperazin-1-yl)phenyl]boronic acidHCID 103197022-[(4-bromophenyl)(pyridin-2-yl)methoxy]-N-(cyanomethyl)-4-methylpentanamide

Product 1

HCID 10345777N-(cyanomethyl)-4-methyl-2-[(4'-piperazin-1-yl-1,1'-biphenyl-4-yl)(pyridin-2-yl)methoxy]pentanamide

Procedure

Using the same protocol as described in example 21, 2-[(4-bromophenyl)(pyridin-2-yl)methoxy]-N-(cyanomethyl)-4-methylpentanamide from example 7, step 4 (241 mg, 0.58 mmol) was coupled with 4-piperazin-1-ylphenylboronic acid (155 mg, 0.64 mmol). The crude residue obtained was chromatographed on silica gel using 1% NH4OH and 9% MeOH in dichloromethane to afford the title compound.

Workup

  1. customThe crude residue obtained
  2. customwas chromatographed on silica gel using 1% NH4OH and 9% MeOH in dichloromethane

Sources & evidence

ORD record
ord-63ba42273a044aa68cb73251b8a012d2
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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