Acetic Anhydride → N-(4-(3-acetamidopiperidin-1-yl)pyridin-3-yl)-3-amino-6-bromopyrazine-2-carboxamide

HRID 69879Notes

Reaction equation

HRID 69879 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([NH:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][C:17]=2[N:18]2[CH2:23][CH2:22][CH2:21][CH:20]([NH2:24])[CH2:19]2)=[O:10])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.C(N(CC)CC)C.[C:32](OC(=O)C)(=[O:34])[CH3:33]>C(Cl)Cl>[C:32]([NH:24][CH:20]1[CH2:21][CH2:22][CH2:23][N:18]([C:17]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[NH:11][C:9]([C:3]2[C:2]([NH2:1])=[N:7][CH:6]=[C:5]([Br:8])[N:4]=2)=[O:10])[CH2:19]1)(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 866691783-amino-N-(4-(3-aminopiperidin-1-yl)pyridin-3-yl)-6-bromopyrazine-2-carboxamide

Product 1

HCID 86669177N-(4-(3-acetamidopiperidin-1-yl)pyridin-3-yl)-3-amino-6-bromopyrazine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To solution of 3-amino-N-(4-(3-aminopiperidin-1-yl)pyridin-3-yl)-6-bromopyrazine-2-carboxamide in CH2Cl2 at a concentration of 0.5 M at room temperature was added triethylamine (3 eq) followed by acetic anhydride (1.2 eq). The reaction was stirred at room temperature for 30 minutes, concentrated, purified by reverse phase HPLC and lyophilized to provide N-(4-(3-acetamidopiperidin-1-yl)pyridin-3-yl)-3-amino-6-bromopyrazine-2-carboxamide, as the TFA salt. LCMS (m/z): 434.1 (MH+).

Workup

  1. concentrationconcentrated
  2. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-d12a126511da4431bd3d642a19543e7f
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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