Sodium Azide → HCID 117600285, compound

HRID 931650Notes

Reaction equation

Br[C:2]1[CH:15]=[C:14]2[C:5]([O:6][C:7]3[C:8]([F:24])=[CH:9][C:10]([O:22][CH3:23])=[CH:11][C:12]=3[C@@:13]32[CH2:20][CH2:19][O:18][C:17]([NH2:21])=[N:16]3)=[CH:4][CH:3]=1.[N-:25]=[N+:26]=[N-:27].[Na+].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].CN[C@@H]1CCCC[C@H]1NC>C(O)C.[Cu]I.O>[N:25]([C:2]1[CH:15]=[C:14]2[C:5]([O:6][C:7]3[C:8]([F:24])=[CH:9][C:10]([O:22][CH3:23])=[CH:11][C:12]=3[C@@:13]32[CH2:20][CH2:19][O:18][C:17]([NH2:21])=[N:16]3)=[CH:4][CH:3]=1)=[N+:26]=[N-:27]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of (S)-7′-bromo-4′-fluoro-2′-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9′-xanthen]-2-amine (422 mg, 1.073 mmol) in ethanol (3.5 ml) was added sodium azide (209 mg, 3.22 mmol), copper(I) iodide (41 mg, 0.215 mmol), (+)-sodium L-ascorbate (21 mg, 0.107 mmol), trans-N,N′-dimethyl-1,2-cyclohexanediamine (0.05 ml, 0.322 mmol) and water (1.5 ml) and the mixture was stirred at 90° C. for 4 hrs. The mixture was cooled to RT, additional water (2 ml) was added and stirring continued for additional 30 min. Precipitated material was filtered off, washed with water twice, and dried under a stream of nitrogen overnight to afford (S)-7′-azido-4′-fluoro-2′-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9′-xanthen]-2-amine (290 mg, 0.816 mmol, 76% yield) which was used without further purification.

Workup

temperatureThe mixture was cooled to RT
stirringstirring
waitcontinued for additional 30 min
filtrationPrecipitated material was filtered off
washwashed with water twice
customdried under a stream of nitrogen overnight

Sources & evidence

ORD record: ord-71e4d4a0290d4195a4828ee1cd4b8da3
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296759B2

Reaction notes

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