N,N-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide → 5-(2-(3,5-Dimethoxyphenethyl)-5H-pyrrolo[2,3-b]pyrazin-6-yl)-N,N-dimethylpicolinamide

HRID 1052279Notes

Reaction equation

HRID 1052279 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.[CH3:23][N:24]([CH3:42])[C:25]([C:27]1[CH:32]=[CH:31][C:30](B2OC(C)(C)C(C)(C)O2)=[CH:29][N:28]=1)=[O:26]>>[CH3:21][O:20][C:14]1[CH:13]=[C:12]([CH:17]=[C:16]([O:18][CH3:19])[CH:15]=1)[CH2:11][CH2:10][C:8]1[N:9]=[C:4]2[CH:3]=[C:2]([C:30]3[CH:31]=[CH:32][C:27]([C:25]([N:24]([CH3:42])[CH3:23])=[O:26])=[N:28][CH:29]=3)[NH:22][C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 57416491N,N-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamideHCID 899624376-Bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 730577595-(2-(3,5-Dimethoxyphenethyl)-5H-pyrrolo[2,3-b]pyrazin-6-yl)-N,N-dimethylpicolinamide

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 N,N-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide (from PepTech Corp. Encyclopedia of Amino Acid Analogs and Boronic Acids). LCMS calculated for C24H26N5O3 (M+H)+: m/z=432.2. Found 432.1.

Workup

  1. customThe compound was prepared

Sources & evidence

ORD record
ord-b452c8b1c90c4f9fbc149ad0c2bf7e3c
Source dataset
uspto-grants-2016_07
Patent number
US09388185B2

Reaction notes

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