O-ethylhydroxylamine hydrochloride → HCID 59258508, compound

HRID 641193Notes

Reaction equation

O=[C:2]1[CH2:7][CH2:6][CH:5]([N:8]2[CH2:13][CH2:12][C:11]3([O:18][C:17](=[O:19])[NH:16][C:15]4[CH:20]=[CH:21][CH:22]=[CH:23][C:14]3=4)[CH2:10][CH2:9]2)[CH2:4][CH2:3]1.Cl.[CH2:25]([O:27][NH2:28])[CH3:26]>N1C=CC=CC=1.CO>[CH2:25]([O:27][N:28]=[C:2]1[CH2:3][CH2:4][CH:5]([N:8]2[CH2:13][CH2:12][C:11]3([O:18][C:17](=[O:19])[NH:16][C:15]4[CH:20]=[CH:21][CH:22]=[CH:23][C:14]3=4)[CH2:10][CH2:9]2)[CH2:6][CH2:7]1)[CH3:26]

Participants

Conditions

Temperature: 60 °C

Procedure

1′-(4-oxocyclohexyl)spiro[benzo[d][1,3]oxazine-4,4′-piperidin]-2(1H)-one (Compound No. 64) (31 mg, 0.10 mmol) was dissolved in anhydrous pyridine (500 μL), treated with of O-ethylhydroxylamine hydrochloride (7 mg, 0.12 mmol) and stirred at 60° C. for 30 minutes. The reaction was cooled to room temperature, diluted with methanol (500 μL) and subjected to reverse-phase HPLC purification (2-30% CH3CN gradient [w/0.1% TFA (aq)] over 10 minutes, 1.0 mL injected, 35 mL/min) to provide 1′-(4-(ethoxyimino)cyclohexyl)spiro[benzo[d][1,3]oxazine-4,4′-piperidin]-2(1H)-one (compound no. 3). LC/MS m/z 358.0 [M+H]+, retention time 1.64 min (RP-C18, 10-99% CH3CN/0.05% TFA).

Workup

temperatureThe reaction was cooled to room temperature
customsubjected to reverse-phase HPLC purification (2-30% CH3CN gradient [w/0.1% TFA (aq)] over 10 minutes, 1.0 mL injected, 35 mL/min)

Sources & evidence

ORD record: ord-25aaf88a8160491dba6a81d0e0c250c0
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696201B2

Reaction notes

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