Pyridine → HCID 54715410, compound

HRID 2109857Notes

Reaction equation

HRID 2109857 reaction equation
[OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=O.[F:8][C:9]1[CH:36]=[CH:35][C:12]([CH2:13][N:14]2[CH2:19][CH2:18][N:17]3[C:20](=[O:33])[C:21]([CH2:26][CH:27]4[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]4)=[C:22]([OH:25])[C:23]([OH:24])=[C:16]3[C:15]2=[O:34])=[CH:11][CH:10]=1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.CN(C=O)C>C(Cl)Cl>[F:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]2[CH2:19][CH2:18][N:17]3[C:20](=[O:33])[C:21]([CH2:26][CH:27]4[CH2:28][CH2:29][N:30]([C:2](=[O:1])[C:4]([F:7])([F:6])[F:5])[CH2:31][CH2:32]4)=[C:22]([OH:25])[C:23]([OH:24])=[C:16]3[C:15]2=[O:34])=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 9845Trifluoroacetic anhydrideHCID 131727396HCID 131727396, compound

Product 1

HCID 54715410HCID 54715410, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-fluorobenzyl)-8,9-dihydroxy-7-(piperidin-4-ylmethyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,6-dione mono TFA salt [50 mg, 0.125 mmol; Example 31 (Step 3)] in methylene chloride (2 mL), pyridine (12 μL, 0.149 mmol), trifluoroacetic anhydride (26 mg, 0.149 mmol) and a couple drops of DMF were added. After one hour, the reaction mixture was concentrated under vacuum, and the residue was purified by prep HPLC [Gilson semi preparative HPLC system using a Waters Nova Pak column (10×40 mm I.D. cartridge, C18, 6 μM pore size) eluting with 95-5% water (0.10% TFA)/acetonitrile (0.10% TFA) gradient at 35 mL/min]. The product fractions were collected and lyophilized to provide the title compound as a white solid.

Workup

  1. concentrationthe reaction mixture was concentrated under vacuum
  2. customthe residue was purified by prep HPLC [Gilson semi preparative HPLC system
  3. washeluting with 95-5% water (0.10% TFA)/acetonitrile (0.10% TFA) gradient at 35 mL/min]
  4. customThe product fractions were collected

Sources & evidence

ORD record
ord-8022da1bcf7942c296071411fad72575
Source dataset
uspto-grants-2009_04
Patent number
US07517532B2

Reaction notes

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