4-(4-BOC-Piperazino)phenylboronic acid → N1-(Cyanomethyl)-N2-[5-Methyl-4-(4-Piperazin-1-ylphenyl)Isoxazol-3-yl]Leucinamide

HRID 1744109Notes

Reaction equation

HRID 1744109 reaction equation
Br[C:2]1[C:3]([NH:8][C@H:9]([C:14]([NH:16][CH2:17][C:18]#[N:19])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[N:4][O:5][C:6]=1[CH3:7].C(OC([N:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=2)[CH2:29][CH2:28]1)=O)(C)(C)C>>[C:18]([CH2:17][NH:16][C:14](=[O:15])[C@H:9]([CH2:10][CH:11]([CH3:13])[CH3:12])[NH:8][C:3]1[C:2]([C:36]2[CH:35]=[CH:34][C:33]([N:30]3[CH2:29][CH2:28][NH:27][CH2:32][CH2:31]3)=[CH:38][CH:37]=2)=[C:6]([CH3:7])[O:5][N:4]=1)#[N:19]

Participants

3

Reactant 2

HCID 52330144-(4-BOC-Piperazino)phenylboronic acidHCID 86594565N2-(4-bromo-5-methylisoxazol-3-yl)-N1-(cyanomethyl)leucinamide

Product 1

HCID 86594566N1-(Cyanomethyl)-N2-[5-Methyl-4-(4-Piperazin-1-ylphenyl)Isoxazol-3-yl]Leucinamide

Procedure

N2-(4-bromo-5-methylisoxazol-3-yl)-N1-(cyanomethyl)leucinamide was treated with 4-[4-(tert-butoxycarbonyl)-1-piperazinyl]phenylboronic acid (prepared as described in Example 1) as described in Example 1 to afford, after BOC removal with methanesulfonic acid as described in Example 1, N1-(cyanomethyl)-N2-[5-methyl-4-(4-piperazin-1-ylphenyl)isoxazol-3-yl]leucinamide. MS (+APCI): 411.4 [M+1]+

Workup

  1. customto afford
  2. customafter BOC removal with methanesulfonic acid

Sources & evidence

ORD record
ord-978bfb20187145bf8f53a5c25c86ba0e
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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