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4-Fluorobenzylamine → Benzyl (2-{[(4-fluorobenzyl)amino]carbonyl}-3-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidin-9-yl)carbamate

HRID 547385
Notes
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Reaction equation

HRID 547385 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:17]2=[N:18][C:19]([C:24](OC)=[O:25])=[C:20]([OH:23])[C:21](=[O:22])[N:16]2[CH:15]=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH2:34])=[CH:31][CH:30]=1>CO>[F:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH:34][C:24]([C:19]2[N:18]=[C:17]3[C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:13][CH:14]=[CH:15][N:16]3[C:21](=[O:22])[C:20]=2[OH:23])=[O:25])=[CH:31][CH:30]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 673264-FluorobenzylamineHCID 54751204Methyl 9-{[(benzyloxy)carbonyl]amino}-3-hydroxy-4-oxo-4-H-pyrido[1,2-a]pyrimidine-2-carboxylate

Product 1

HCID 86761308Benzyl (2-{[(4-fluorobenzyl)amino]carbonyl}-3-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidin-9-yl)carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of methyl 9-{[(benzyloxy)carbonyl]amino}-3-hydroxy-4-oxo-4-H-pyrido[1,2-a]pyrimidine-2-carboxylate in MeOH was added p-fluorobenzylamine. The suspension was stirred at 80° C. and after 16 hours the solvent was removed under reduced pressure. The product was purified by preparative RP-HPLC, using water (0.1% TFA) and acetonitrile (0.1% TFA) as eluants (column: C18). The product was obtained after lyophilization of the pooled product fractions as bright yellow fluffy material.

Workup

  1. customwas removed under reduced pressure
  2. customThe product was purified by preparative RP-HPLC
  3. customThe product was obtained after lyophilization of the pooled product fractions as bright yellow fluffy material

Sources & evidence

ORD record
ord-45db45cb4c164866a970a26e573cbc9f
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07939537B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes