1-Methyl-4-piperidone → 3-amino-6-bromo-N-(4-(3-(1-methylpiperidin-4-ylamino)piperidin-1-yl)pyridin-3-yl)pyrazine-2-carboxamide

HRID 69890

Reaction equation

HRID 69890 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.[CH3:25][N:26]1[CH2:31][CH2:30][C:29](=O)[CH2:28][CH2:27]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[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]([NH:24][CH:29]3[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][CH2:28]3)[CH2:19]2)=[O:10])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 740491-Methyl-4-piperidoneHCID 5049666Sodium triacetoxyborohydrideHCID 866691783-amino-N-(4-(3-aminopiperidin-1-yl)pyridin-3-yl)-6-bromopyrazine-2-carboxamide

Product 1

HCID 866691883-amino-6-bromo-N-(4-(3-(1-methylpiperidin-4-ylamino)piperidin-1-yl)pyridin-3-yl)pyrazine-2-carboxamideYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-amino-N-(4-(3-aminopiperidin-1-yl)pyridin-3-yl)-6-bromopyrazine-2-carboxamide in CH2Cl2 at room temperature was added 1-methylpiperidin-4-one (1.5 eq) followed by sodium triacetoxyborohydride (5.0 eq). The reaction was stirred at room temperature for 12 hours, concentrated, purified by reverse phase HPLC and lyophilized to provide 3-amino-6-bromo-N-(4-(3-(1-methylpiperidin-4-ylamino)piperidin-1-yl)pyridin-3-yl)pyrazine-2-carboxamide, (66%). LCMS (m/z): 489.2 (MH+).

Workup

  1. concentrationconcentrated
  2. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-a9fea1ac95f241c4858ab8725b7ddc2b
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Linked notes

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