Pyridine → HCID 54710418, compound

HRID 2109853Notes

Reaction equation

HRID 2109853 reaction equation
[OH:1][C:2]([C:4](F)(F)F)=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.C(OC(=O)C)(=O)C>C(Cl)Cl>[C:2]([N:30]1[CH2:29][CH2:28][CH:27]([CH2:26][C:21]2[C:20](=[O:33])[N:17]3[CH2:18][CH2:19][N:14]([CH2:13][C:12]4[CH:11]=[CH:10][C:9]([F:8])=[CH:36][CH:35]=4)[C:15](=[O:34])[C:16]3=[C:23]([OH:24])[C:22]=2[OH:25])[CH2:32][CH2:31]1)(=[O:1])[CH3:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 131727396HCID 131727396, compound

Product 1

HCID 54710418HCID 54710418, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension 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) in anhydrous methylene chloride (2 mL), pyridine (12 μL, 0.149 mmol) and acetic anhydride (14 μL, 0.149 mmol) were added. The reaction mixture was stirred at room temperature overnight. 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% TPA)/acetonitrile (0.10% TFA) gradient at 35 mL/min]. Collection and lyophilization of appropriate fractions provided he title compound as white solid.

Workup

  1. additionwere added
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. customthe residue was purified by prep HPLC (Gilson semi preparative HPLC system
  4. washcartridge, C18, 6 μM pore size) eluting with 95-5% water (0.10% TPA)/acetonitrile (0.10% TFA) gradient at 35 mL/min]
  5. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-0243612913a64e52920c71349e9b7b6a
Source dataset
uspto-grants-2009_04
Patent number
US07517532B2

Reaction notes

Loading…