4-((5-(Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)methyl)morpholine → 2-Amino-N-(3-chloro-pyridin-4-yl)-5-(5-morpholin-4-ylmethyl-thiophen-2-yl)-nicotinamide

HRID 919233Notes

Reaction equation

HRID 919233 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[Cl:17])=[O:9])=[CH:6][C:5](Br)=[CH:4][N:3]=1.[N:19]1([CH2:25][C:26]2[S:30][C:29](B3OC(C)(C)C(C)(C)O3)=[CH:28][CH:27]=2)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:29]2[S:30][C:26]([CH2:25][N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)=[CH:27][CH:28]=2)=[CH:6][C:7]=1[C:8]([NH:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[Cl:17])=[O:9]

Participants

3

Reactant 2

HCID 467390464-((5-(Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)methyl)morpholineHCID 710608052-amino-5-bromo-N-(3-chloro-4-pyridyl)pyridine-3-carboxamide

Product 1

HCID 710612592-Amino-N-(3-chloro-pyridin-4-yl)-5-(5-morpholin-4-ylmethyl-thiophen-2-yl)-nicotinamide

Procedure

Reaction of 2-amino-5-bromo-N-(3-chloro-4-pyridyl)pyridine-3-carboxamide with 5-(4-morpholinylmethyl)thiophene-2-boronic acid pinacol ester gives the compound “A33”; HPLC/MS: 1.25 min, [M+H]=343;

Workup

  1. customgives the compound “A33”
  2. custom1.25 min, [M+H]=343

Sources & evidence

ORD record
ord-4290fb889db54aa2adaf297c7e78d644
Source dataset
uspto-grants-2016_03
Patent number
US09273029B2

Reaction notes

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