Tetrahydrofuran → 3-aminomethyl-2-oxazol-2-yl-1-phenyl-1H-[1, 8]naphthyridin-4-one bis(tert-butyl carbamate)

HRID 1887787Notes

Reaction equation

Br[CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:4]=1[C:20]1[O:21][CH:22]=[CH:23][N:24]=1.[CH2:25]1[CH2:29]OC[CH2:26]1.[NH:30](C(OC(C)(C)C)=O)[C:31]([O:33]C(C)(C)C)=[O:32].[H-].[Na+]>[Cl-].[NH4+].CN(C=O)C>[C:25]([NH:30][C:31](=[O:32])[OH:33])([CH3:26])([CH3:29])[CH3:2].[C:25]([NH:30][C:31](=[O:32])[OH:33])([CH3:26])([CH3:29])[CH3:2].[NH2:30][CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:4]=1[C:20]1[O:21][CH:22]=[CH:23][N:24]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a mixture of 3-bromomethyl-2-oxazol-2-yl-1-phenyl-1H-[1,8]naphthyridin-4-one (320 mg, 0.837 mmol), THF (2.79 mL) and DMF (2.79 mL) was added di-tert-butyl iminodicarboxylate (182 mg, 0.837 mmol) and sodium hydride (60% in mineral oil, 33.5 mg, 0.837 mmol). The reaction mixture was heated at 45° C. overnight which turned into a clear yellow solution. The reaction was diluted with a saturated aqueous ammonium chloride solution (30 mL) and was extracted into methylene chloride (3×50 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. Flash chromatography (30%-50% ethyl acetate-hexanes) afforded 3-aminomethyl-2-oxazol-2-yl-1-phenyl-1H-[1,8]naphthyridin-4-one bis(tert-butyl carbamate) (298.7 mg, 68.8%) as an off-white solid.

Workup

extractionwas extracted into methylene chloride (3×50 mL)
dry with materialThe combined organic layers were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-43b3672243204acd8e3f92fc38cb9097
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501732B2

Reaction notes

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