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

HRID 547385Notes

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

Participants

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

customwas removed under reduced pressure
customThe product was purified by preparative RP-HPLC
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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