Hydroxylamine → HCID 44554073, compound

HRID 1254053Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:11][C:10]=2[C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)=[CH:4][CH:3]=1.O[NH2:30].[C:31]([O-:34])([O-])=O.[K+].[K+]>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:11][C:10]=2[C:21]2[CH:22]=[CH:23][C:24]([C:25]3[N:30]=[CH:31][O:34][N:26]=3)=[CH:27][CH:28]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To 4-{5-[(4-chlorophenyl)thio]-1-methyl-2-phenyl-1H-imidazol-4-yl}benzonitrile (Example 2, 30 mg, 0.075 mmol) in 2 mL EtOH was added 0.25 mL of HONH2 and catalytic amount of K2CO3. The reaction was heated at 120° C. for 60 min via microwave. The reaction mixture was concentrated to dryness and the residue was dissolved in 5 mL triethylorthoformate. 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 the title compound. 1H NMR (500 MHz, (CDCl3): 8.74 (s, 1H), 8.27 (d, 2H), 8.18 (d, 2H), 7.72 (m, 2H), 7.53 (m, 3H), 7.25 (d, 2H), 7.06 (d, 2H), 3.68 (s, 3H). LCMS: m/z 445 (M+H)+.

Workup

concentrationThe reaction mixture was concentrated to dryness
dissolutionthe residue was dissolved in 5 mL triethylorthoformate
additionCatalytic 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-3e939911cb9143e2a34fe450d760ab17
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455528B2

Reaction notes

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