Hydroxylamine → HCID 44815805, compound

HRID 1187436Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=2)=[CH:4][CH:3]=1.[NH2:28]O.[C:30]([O-:33])([O-])=O.[K+].[K+]>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:20]2[CH:21]=[CH:22][C:23]([C:24]3[N:28]=[CH:30][O:33][N:25]=3)=[CH:26][CH:27]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To 3-(4-{5-[(4-chlorophenyl)thio]-2-phenyl-1,3oxazol-4-yl}benzonitrile (30 mg, 0.075 mmol) in 2 mL EtOH was added 0.25 mL of 50% aqueous NH2OH and catalytic amount of K2CO3. The reaction was heated at 120° C. for 1 h via microwave irradiation. The reaction mixture was concentrated to dryness and the residue was dissolved in 5 mL triethylorthoformate. A catalytic amount of TFA was added, and the reaction was heated at 130° C. for 3 h. The volatiles were removed and the residue was purified by reverse phase HPLC to afford 12 mg (37% yield) of the title compound: m/z 432.1 (M+H)+. 1H NMR (500 MHz, CDCl3: δ 8.8 (1H, s), 8.39 (2H, d), 8.21 (2H, d), 8.19 (1H, m), 7.59 (4H, br), 7.24 (4H, br).

Workup

concentrationThe reaction mixture was concentrated to dryness
dissolutionthe residue was dissolved in 5 mL triethylorthoformate
additionA catalytic amount of TFA was added
temperaturethe reaction was heated at 130° C. for 3 h
customThe volatiles were removed
customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-b71781da230d4d7291aa17bd3af48d19
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673941B2

Reaction notes

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