HCID 11984296, compound → HCID 21069968, compound

HRID 348181Notes

Reaction equation

HRID 348181 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](O)=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:25][CH2:26][C:27]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:28]=1[C:29]([O:31][CH3:32])=[O:30]>>[CH2:1]([O:8][C:9]1[C:18](=[O:19])[N:17]2[C:12]([C:13]([CH3:20])([CH3:21])[O:14][CH2:15][CH2:16]2)=[N:11][C:10]=1[C:22]([NH:25][CH2:26][C:27]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:28]=1[C:29]([O:31][CH3:32])=[O:30])=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 11984296HCID 11984296, compoundHCID 210698583-(Benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylic acid

Product 1

HCID 21069968HCID 21069968, 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 intermediate 38, methyl 2-(aminomethyl)-5-fluorobenzoate. 1H NMR (CDCl3, 500 MHz) δ ppm: 1.61 (6H, s, gem-Me), 3.88 (3H, s, OMe), 3.97 (2H, t, J=5.5 Hz, CH2), 4.02 (2H, t, J=5.5 Hz, CH2), 4.73 (2H, d, J=6.7 Hz, NCH2), 5.25 (2H, s, OCH2), 7.19 (1H, dt, J=3, 8.5 Hz, Ar—H), 7.27–7.31 (3H, m, Ar—Hs), 7.48–7.50 (2H, m, Ar—Hs), 7.61 (1H, dd, J=5.5, 8.5 Hz, Ar—H), 7.66 (1H, dd, J=3, 9.5 Hz, Ar—H). LC/MS m/z 496 (M+H).

Sources & evidence

ORD record
ord-318aa9fbb0e0408196c767f98d2cb7e8
Source dataset
uspto-grants-2007_02
Patent number
US07176196B2

Reaction notes

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