4-Fluorobenzylamine → N-(4-Fluorobenzyl)-3-(benzyloxy)-9-methyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxamide

HRID 348178Notes

Reaction equation

HRID 348178 reaction equation
[CH2:1]([O:8][C:9]1[C:18](=[O:19])[N:17]2[C:12]([CH:13]([CH3:20])[O:14][CH2:15][CH2:16]2)=[N:11][C:10]=1[C:21]([OH:23])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1>>[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH:30][C:21]([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:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:16][CH2:15][O:14][CH:13]3[CH3:20])=[O:23])=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 673264-FluorobenzylamineHCID 210698603-Benzyloxy-9-methyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylic acid

Product 1

HCID 21070030N-(4-Fluorobenzyl)-3-(benzyloxy)-9-methyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxamide

Procedure

The title compound can be prepared from intermediate 16, 3-benzyloxy-9-methyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylic acid and 4-fluorobenzylamine. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.67 (3H, d, J=6.6 Hz, CH3), 3.91 (2H, m, CH2), 4.12–4.35 (2H, m, CH2), 4.52 (2H, d, J=5.9 Hz, NCH2), 4.70 (1H, q, J=6.6 Hz, OCH), 5.33 (2H, s, OCH2), 7.02 (2H, m, aromatics), 7.25 (2H, m, aromatics), 7.35 (3H, m, aromatics), 7.47 (2H, m, aromatics), 7.71 (1H, broad t, NH).

Sources & evidence

ORD record
ord-62f59afc3f9c42fcbacfc8937b1adcd8
Source dataset
uspto-grants-2007_02
Patent number
US07176196B2

Reaction notes

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