4-Fluorobenzylamine → n-(4-Fluorobenzyl)-5-hydroxy-1-methyl-6-oxo-2-[1-(pyridin-2-ylcarbonyl)-1,2,3,4-tetrahydroquinolin-2-yl]-1,6-dihydropyrimidine-4-carboxamide

HRID 1161912Notes

Reaction equation

C([O:9][C:10]1[C:15](=[O:16])[N:14]([CH3:17])[C:13]([CH:18]2[CH2:27][CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]2[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)=[O:29])=[N:12][C:11]=1[C:36](OC)=[O:37])(=O)C1C=CC=CC=1.[F:40][C:41]1[CH:48]=[CH:47][C:44]([CH2:45][NH2:46])=[CH:43][CH:42]=1>CN(C=O)C>[F:40][C:41]1[CH:48]=[CH:47][C:44]([CH2:45][NH:46][C:36]([C:11]2[N:12]=[C:13]([CH:18]3[CH2:27][CH2:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]3[C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=3)=[O:29])[N:14]([CH3:17])[C:15](=[O:16])[C:10]=2[OH:9])=[O:37])=[CH:43][CH:42]=1

Participants

Conditions

Temperature: 90 °C

Procedure

The residue of Step 2 was dissolved in DMF and 4-fluorobenzylamine (3 eq.) was added. The reaction mixture was stirred at 90° C. for 1 h. The title compound was purified by preparative HPLC and isolated as its trifluoroacetic salt (C18, gradient of CH3CN/H2O+0.01% TFA).

Workup

customThe title compound was purified by preparative HPLC
customisolated as its trifluoroacetic salt (C18, gradient of CH3CN/H2O+0.01% TFA)

Sources & evidence

ORD record: ord-a3662435108f4dd7b3d365e56d346d82
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820660B2

Reaction notes

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