1-(2-Methoxyethyl)-1H-pyrazole-4-boronic acid, pinacol ester → 2-Amino-5-[1-(2-methoxy-ethyl)-1H-pyrazol-4-yl]-N-(3-methyl-pyridin-4-yl)-nicotinamide

HRID 919222Notes

Reaction equation

HRID 919222 reaction equation
[NH2:1][C:2]1[N:17]=[CH:16][C:15](Br)=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[CH3:13])=[O:5].[CH3:19][O:20][CH2:21][CH2:22][N:23]1[CH:27]=[C:26](B2OC(C)(C)C(C)(C)O2)[CH:25]=[N:24]1>>[NH2:1][C:2]1[N:17]=[CH:16][C:15]([C:26]2[CH:25]=[N:24][N:23]([CH2:22][CH2:21][O:20][CH3:19])[CH:27]=2)=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[CH3:13])=[O:5]

Participants

3

Reactant 2

HCID 112304911-(2-Methoxyethyl)-1H-pyrazole-4-boronic acid, pinacol esterHCID 636703852-amino-5-bromo-N-(3-methylpyridin-4-yl)nicotinamide

Product 1

HCID 710611192-Amino-5-[1-(2-methoxy-ethyl)-1H-pyrazol-4-yl]-N-(3-methyl-pyridin-4-yl)-nicotinamide

Procedure

Reaction of 2-amino-5-bromo-N-(3-methyl-pyridin-4-yl)-nicotinamide with 1-(2-methoxy-ethyl)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole gives the compound “A22”; HPLC/MS: 1.07 min, [M+H]=353;

Workup

  1. customgives the compound “A22”
  2. custom1.07 min, [M+H]=353

Sources & evidence

ORD record
ord-452bd97fadcb4e1581653780e91592b1
Source dataset
uspto-grants-2016_03
Patent number
US09273029B2

Reaction notes

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