[4-(Piperazin-1-yl)phenyl]boronic acid → N-(cyanomethyl)-4-methyl-2-[(4'-piperazin-1-yl-1,1'-biphenyl-4-yl)(1,3-thiazol-2-yl)methoxy]pentanamide

HRID 1180406Notes

Reaction equation

HRID 1180406 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:21]2[S:22][CH:23]=[CH:24][N:25]=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:26]1([C:32]2[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=2)[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]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:35]2[CH:34]=[CH:33][C:32]([N:26]3[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]3)=[CH:37][CH:36]=2)=[CH:3][CH:4]=1)[C:21]1[S:22][CH:23]=[CH:24][N:25]=1)[CH2:17][CH:18]([CH3:20])[CH3:19])#[N:16]

Participants

3

Reactant 2

HCID 5233013[4-(Piperazin-1-yl)phenyl]boronic acidHCID 103200442-[(4-bromophenyl)(1,3-thiazol-2-yl)methoxy]-N-(cyanomethyl)-4-methylpentanamide

Product 1

HCID 10391401N-(cyanomethyl)-4-methyl-2-[(4'-piperazin-1-yl-1,1'-biphenyl-4-yl)(1,3-thiazol-2-yl)methoxy]pentanamide

Procedure

Using the same protocol as described in example 21, 2-[(4-bromophenyl)(1,3-thiazol-2-yl)methoxy]-N-(cyanomethyl)-4-methylpentanamide from example 27, step 4 (225 mg, 0.53 mmol) was coupled with 4-piperazin-1-ylphenylboronic acid (141 mg, 0.58 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-81e89496c4234227a4a96288e22b30eb
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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