Hydroxyamine hydrochloride → HCID 51347784, compound

Reaction equation

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

Participants

Procedure

1 ml dry MeOH was added to 2-(3,5-dimethylisoxazol-4-yl)-3-(4-hydroxyphenyl)-1H-indole-1-carbonitrile (Example 1, 4.5 mg, 0.01 mmol) under nitrogen followed by 10 eq hydroxylamine hydrochloride. 10 eq NaOMe was added and the mixture was stirred for 4 h. The solvent was concentrated and the crude product was purified on silica using CH2Cl2/MeOH (97:3 to 96:4) as eluents. 2.10 mg 2-(3,5-dimethylisoxazol-4-yl)-N′-hydroxy-3-(4-hydroxyphenyl)-1H-indole-1-carboximidamide (E2) ES/MS m/z: 363.5 (M+H), 361.6 (M−H); 1H NMR (MeOD, 500 MHz): 7.65 (m 1H), 7.60 (m, 1H), 7.29 (m, 1H), 7.18 (m, 1H), 7.12 (m, 2H), 6.79 (m, 2H), 2.12 (s, 3H), 1.99 (s, 3H) and 1.90 mg 2-(3,5-dimethylisoxazol-4-yl)-3-(4-hydroxyphenyl)-1H-indole-1-carboxamide (E3) ES/MS m/z: 348.2 (M+H), 346.3 (M−H); 1H NMR (MeOD, 500 MHz): 7.93 (m 1H), 7.61 (m, 1H), 7.35 (m, 1H), 7.23 (m, 1H), 7.08 (m, 2H), 6.81 (m, 2H), 2.07 (s, 3H), 2.03 (s, 3H) were obtained as white solids. For Example 2, the title compound was identified by 1H-NMR which showed that the oxime product was a single isomer, but did not confirm whether the (E) or (Z) oxime isomer had been obtained.