3-(Benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylic acid → HCID 21069994, compound

HRID 1788196Notes

Reaction equation

HRID 1788196 reaction equation
[CH2:1]([O:8][C:9]1[C:18](=[O:19])[N:17]2[C:12]([C:13]([CH3:21])([CH3:20])[O:14][CH2:15][CH2:16]2)=[N:11][C:10]=1[C:22]([OH:24])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][NH2:33])=[C:28]([C:34]2[N:35]=[N:36][S:37][CH:38]=2)[CH:27]=1>>[F:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][NH:33][C:22]([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][C:13]3([CH3:20])[CH3:21])=[O:24])=[C:28]([C:34]2[N:35]=[N:36][S:37][CH:38]=2)[CH:27]=1

Participants

3

Reactant 2

HCID 210698583-(Benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylic acidHCID 21069873HCID 21069873, compound

Product 1

HCID 21069994HCID 21069994, compound

Procedure

The title compound can be prepared from intermediate 27, 3-(benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido-[2,1-c][1,4]oxazine-2-carboxylic acid and (4-fluoro-2-(1,2,3-thiadiazol-4-yl)phenyl)methanamine. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.66 (6H, s, 2×CH3), 4.02 (4H, m, 2×CH2), 4.57 (2H, d, J=6.6 Hz, NCH2), 5.32 (2H, s, OCH2), 7.18 (1H, m, aromatic), 7.27-7.34 (4H, m, aromatics), 7.54 (2H, m, aromatics), 7.74 (1 H, dd, J=6.2 Hz and J=8.6 Hz, aromatic), 8.71 (1 H, s, CH), 8.80 (1H, broad t, NH). HRMS (ESI+) calculated for C26H25FN5O4S [M+H+]: 522.1611: found: 522.1601.

Sources & evidence

ORD record
ord-fece3a4ae2524d2788228ac1c7f850b8
Source dataset
uspto-grants-2009_03
Patent number
US07511037B2

Reaction notes

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