1-((5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)methyl)pyrrolidine → 3-Amino-6-(5-pyrrolidin-1-ylmethyl-thiophen-2-yl)-pyrazine-2-carboxylic acid pyridin-4-ylamide

HRID 919216Notes

Reaction equation

HRID 919216 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]([C:10]2[C:15]([NH2:16])=[N:14][CH:13]=[C:12](Br)[N:11]=2)=[O:9])=[CH:3][CH:2]=1.CC1(C)C(C)(C)OB([C:26]2[S:30][C:29]([CH2:31][N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)=[CH:28][CH:27]=2)O1>>[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]([C:10]2[C:15]([NH2:16])=[N:14][CH:13]=[C:12]([C:26]3[S:30][C:29]([CH2:31][N:32]4[CH2:36][CH2:35][CH2:34][CH2:33]4)=[CH:28][CH:27]=3)[N:11]=2)=[O:9])=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 467397461-((5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)methyl)pyrrolidineHCID 867191543-Amino-6-bromo-N-4-pyridinyl-2-pyrazinecarboxamide

Product 1

HCID 710611123-Amino-6-(5-pyrrolidin-1-ylmethyl-thiophen-2-yl)-pyrazine-2-carboxylic acid pyridin-4-ylamide

Procedure

The reaction of 3-amino-6-bromo-pyrazine-2-carboxylic acid pyridin-4-ylamide (synthesis described for “A10”) with 1-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-thiophen-2-ylmethyl]-pyrrolidine gives the compound “A14”;

Workup

  1. customgives the compound “A14”

Sources & evidence

ORD record
ord-25ef332c7b2c40809243f12738345680
Source dataset
uspto-grants-2016_03
Patent number
US09273029B2

Reaction notes

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