Morpholine → HCID 54682263, compound

HRID 2426259Notes

Reaction equation

HRID 2426259 reaction equation
C([O:9][C:10]1[C:15](=[O:16])[N:14]2[CH2:17][CH2:18][CH2:19][CH:20](Br)[C:13]2=[N:12][C:11]=1[C:22]([O:24]C)=O)(=O)C1C=CC=CC=1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.[F:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37][NH2:38])=[CH:35][CH:34]=1>CN(C=O)C>[F:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37][NH:38][C:22]([C:11]2[N:12]=[C:13]3[CH:20]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[CH2:19][CH2:18][CH2:17][N:14]3[C:15](=[O:16])[C:10]=2[OH:9])=[O:24])=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 673264-FluorobenzylamineHCID 67147765HCID 67147765, compound

Product 1

HCID 54682263HCID 54682263, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 3-(benzoyloxy)-9-bromo-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-2-carboxylate in DMF was added morpholine (3 eq.) and the mixture was stirred at room temperature for 1 h. The solvent was removed under reduced pressure and the residue was triturated with diethyl ether. The crude material was dissolved in methanol, 4-fluoro-benzylamine (3 eq.) was added and the mixture was stirred for 1.5 h at 65° C. The solvent was removed under reduced pressure and the product was purified by preparative RP-HPLC, using water (0.1% TFA) and acetonitrile (0.1% TFA) as eluents (column: C18). The pooled product fractions were lyophilized and redissolved in 1N HCl. The solvent was removed under reduced pressure and the residue was lyophilized from water/acetonitrile to afford the hydrochloride salt of N-(4-fluorobenzyl)-3-hydroxy-9-morpholin-4-yl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-2-carboxamide as a slightly pink fluffy material.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was triturated with diethyl ether
  3. dissolutionThe crude material was dissolved in methanol
  4. stirringthe mixture was stirred for 1.5 h at 65° C
  5. customThe solvent was removed under reduced pressure
  6. customthe product was purified by preparative RP-HPLC
  7. dissolutionredissolved in 1N HCl
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0c4994b317f74bfd90c38d97c0054a25
Source dataset
uspto-grants-2011_06
Patent number
US07968553B2

Reaction notes

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