Cyclopropanecarboxaldehyde → HCID 131727397, compound

HRID 2109858Notes

Reaction equation

HRID 2109858 reaction equation
[OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=[O:3].[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][CH2:30][NH: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.[CH:37]1([CH:40]=O)[CH2:39][CH2:38]1.C([BH3-])#N.[Na+]>CO>[OH:3][C:2]([C:4]([F:7])([F:6])[F:5])=[O:1].[CH:37]1([CH2:40][N:29]2[CH2:30][CH2:31][CH2:32][CH:27]([CH2:26][C:21]3[C:20](=[O:33])[N:17]4[CH2:18][CH2:19][N:14]([CH2:13][C:12]5[CH:11]=[CH:10][C:9]([F:8])=[CH:36][CH:35]=5)[C:15](=[O:34])[C:16]4=[C:23]([OH:24])[C:22]=3[OH:25])[CH2:28]2)[CH2:39][CH2:38]1

Participants

5

Reactant 3

HCID 123114CyclopropanecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 131727398HCID 131727398, compound

Product 1

HCID 131727397HCID 131727397, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(4-fluorobenzyl)-8,9-dihydroxy-7-(piperidin-3-ylmethyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,6-dione mono TFA salt (50 mg, 0.097 mmol) in anhydrous methanol (2 mL) under nitrogen, cyclopropanecarboxaldehyde (9 μL, 0.116mmol) was added and the solution was stirred at room temperature for one hour. Sodium cyanoborohydride (8 mg, 0.129 mmol) was added and the solution was stirred for another 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 white solid.

Workup

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

Sources & evidence

ORD record
ord-02ea93adba9f40db877b3102196f0ccd
Source dataset
uspto-grants-2009_04
Patent number
US07517532B2

Reaction notes

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