2-(aminomethyl)-5-fluoro-N-methylbenzamide → N-(4-Fluoro-2-(methylcarbamoyl)benzyl)-3-(benzyloxy)-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxamide

HRID 1372285Notes

Reaction equation

HRID 1372285 reaction equation
[CH2:1]([O:8][C:9]1[C:18](=[O:19])[N:17]2[C:12]([CH2:13][O:14][CH2:15][CH2:16]2)=[N:11][C:10]=1[C:20]([OH:22])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:23][CH2:24][C:25]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:26]=1[C:27]([NH:29][CH3:30])=[O:28]>>[F:35][C:32]1[CH:33]=[CH:34][C:25]([CH2:24][NH:23][C:20]([C:10]2[N:11]=[C:12]3[N:17]([C:18](=[O:19])[C:9]=2[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:16][CH2:15][O:14][CH2:13]3)=[O:22])=[C:26]([C:27](=[O:28])[NH:29][CH3:30])[CH:31]=1

Participants

3

Reactant 2

HCID 112753932-(aminomethyl)-5-fluoro-N-methylbenzamideHCID 210698563-(Benzyloxy)-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylic acid

Product 1

HCID 21070021N-(4-Fluoro-2-(methylcarbamoyl)benzyl)-3-(benzyloxy)-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxamide

Procedure

The title compound can be prepared from intermediate 7, 3-(benzyloxy)-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylic acid and intermediate 39, 2-(aminomethyl)-5-fluoro-N-methylbenzamide. White crystals; mp 189–190° C. (ethyl acetate). 1HNMR 400 MHz (CDCl3) δ (ppm): 3.01 (3H, d, J=4.5 Hz, NCH3), 4.00 (2H, m, CH2), 4.08 (1H, m, CH), 4.50 (2H, d, J=6.6 Hz, NCH2), 4.71 (2H, s, OCH2), 5.38 (2H, s, OCH2), 6.88 (1H, broad q, NH), 7.07 (1H, m, aromatic), 7.16 (1H, dd, J=2.5 Hz and J=8.6 Hz, aromatic), 7.30–7.44 (6H, m, aromatics), 8.55 (1H, broad t, NH). Anal. Calcd for C24H23FN4O5: C, 61.80; H, 4.97; N, 12.01. Found: C, 61.84; H, 4.82; N, 12.00.

Sources & evidence

ORD record
ord-872c1532bb7549149fc12af12c7bc8d3
Source dataset
uspto-grants-2007_01
Patent number
US07157447B2

Reaction notes

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