Lithium hydroxide, monohydrate → HCID 58577796, compound

HRID 473971Notes

Reaction equation

O.[OH-].[Li+].[NH2:4][C:5]1[C:10]2[C:11](=[O:31])[N:12]([C:16]3[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]([CH3:30])([CH3:29])[C:25]([O:27]C)=[O:26])=[N:20][CH:21]=3)[CH2:13][CH2:14][O:15][C:9]=2[N:8]=[CH:7][N:6]=1>O1CCOCC1.O>[NH2:4][C:5]1[C:10]2[C:11](=[O:31])[N:12]([C:16]3[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]([CH3:29])([CH3:30])[C:25]([OH:27])=[O:26])=[N:20][CH:21]=3)[CH2:13][CH2:14][O:15][C:9]=2[N:8]=[CH:7][N:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Lithium hydroxide monohydrate (16.4 mg, 0.39 mmol) was added at room temperature to a solution of methyl 3-(5-(4-amino-5-oxo-7,8-dihydropyrimido[5,4-f][1,4]oxazepin-6(5H)-yl)pyridin-2-yloxy)-2,2-dimethylpropanoate B-21 (50.4 mg, 0.13 mmol) in 1,4-dioxane (2.0 mL) and water (1.0 mL). The reaction mixture was heated at 60° C. for 2 h and then concentrated to dryness under reduced pressure. The residue was purified by flash column chromatography on C18 reverse phase (water:acetonitrile gradient with 0.05% formic acid) to give 3-(5-(4-amino-5-oxo-7,8-dihydropyrimido[5,4-f][1,4]oxazepin-6(5H)-yl)pyridin-2-yloxy)-2,2-dimethylpropanoic acid B-22 (27.0 mg, Yield=56%). 1H NMR (500 MHz, METHANOL-d4) δ ppm 1.33 (s, 6H), 4.13 (m, 2H), 4.35 (s, 2H), 4.85 (m, 2H), 6.90 (d, J=8.83 Hz, 1H), 7.71 (d, J=8.83 Hz, 1H), 8.16 (s, 1H), 8.29 (s, 1H); MS (ESI) [M+1]+ 374.

Workup

concentrationconcentrated to dryness under reduced pressure
customThe residue was purified by flash column chromatography on C18 reverse phase (water:acetonitrile gradient with 0.05% formic acid)

Sources & evidence

ORD record: ord-59195da2d3fe47c0b9e136bacd923153
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637507B2

Reaction notes

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