Water → HCID 58777355, compound

HRID 348219Notes

Reaction equation

CS(O[CH2:6][C@H:7]1[CH2:11][CH2:10][C:9](=[O:12])[N:8]1[C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[CH2:20][NH:21][C:22]([C:24]1[N:25]=[C:26]2[N:31]([C:32](=[O:42])[C:33]=1[O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:30][CH2:29][O:28][C:27]2([CH3:44])[CH3:43])=[O:23])(=O)=O.[N-:45]=[N+:46]=[N-:47].[Na+].O>CN(C=O)C>[N:45]([CH2:6][C@H:7]1[CH2:11][CH2:10][C:9](=[O:12])[N:8]1[C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[CH2:20][NH:21][C:22]([C:24]1[N:25]=[C:26]2[N:31]([C:32](=[O:42])[C:33]=1[O:34][CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[CH2:30][CH2:29][O:28][C:27]2([CH3:43])[CH3:44])=[O:23])=[N+:46]=[N-:47]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of intermediate 194, (R)-(1-(2-((3-(benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxamido)methyl)-5-fluorophenyl)-5-oxopyrrolidin-2-yl)methyl methanesulfonate (0.150 g, 0.239 mmol) in DMF (10 mL) was added sodium azide (0.019 g, 0.287 mmol). The resulting mixture was stirred at 50° C. for 6 h. Water (50 mL) was then added and the organic material was extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with H2O (50 mL), dried (MgSO4), filtered and concentrated in vacuo to afford the title compound (0.125 g, 91% yield). LCMS (M+H)+ m/z 576.

Workup

extractionthe organic material was extracted with ethyl acetate (2×50 mL)
washThe combined organic extracts were washed with H2O (50 mL)
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-745e340cc72e4c2cbff84455007fd8f9
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07176196B2

Reaction notes

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