(3-Chloro-4-(dimethylcarbamoyl)phenyl)boronic acid → 2-Chloro-4-(2-(3,5-dimethoxyphenethyl)-5H-pyrrolo[2,3-b]pyrazin-6-yl)-N,N-dimethylbenzamide

HRID 1052276Notes

Reaction equation

HRID 1052276 reaction equation
Br[C:2]1[NH:22][C:5]2=[N:6][CH:7]=[C:8]([CH2:10][CH2:11][C:12]3[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[CH:13]=3)[N:9]=[C:4]2[CH:3]=1.[Cl:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][C:29]=1[C:30](=[O:34])[N:31]([CH3:33])[CH3:32]>>[Cl:23][C:24]1[CH:25]=[C:26]([C:2]2[NH:22][C:5]3=[N:6][CH:7]=[C:8]([CH2:10][CH2:11][C:12]4[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[CH:13]=4)[N:9]=[C:4]3[CH:3]=2)[CH:27]=[CH:28][C:29]=1[C:30]([N:31]([CH3:33])[CH3:32])=[O:34]

Participants

3

Reactant 2

HCID 44119415(3-Chloro-4-(dimethylcarbamoyl)phenyl)boronic acidHCID 899624376-Bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 730574642-Chloro-4-(2-(3,5-dimethoxyphenethyl)-5H-pyrrolo[2,3-b]pyrazin-6-yl)-N,N-dimethylbenzamide

Procedure

The compound was prepared by using procedures analogous to those described for the synthesis of Example 53, Step 2 starting from 6-bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-5H-pyrrolo[2,3-b]pyrazine and 3-chloro-4-(dimethylcarbamoyl)phenylboronic acid (from Combi-Blocks). LCMS calculated for C25H26ClN4O3 (M+H)+: m/z=465.2. Found 465.1.

Workup

  1. customThe compound was prepared

Sources & evidence

ORD record
ord-048d2f87c4c24dcab3dc1c933d99268b
Source dataset
uspto-grants-2016_07
Patent number
US09388185B2

Reaction notes

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