Hydroxyamine hydrochloride → HCID 51347784, compound

HRID 2370987Notes

Reaction equation

HRID 2370987 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

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 51347782HCID 51347782, compound

Product 1

HCID 51347784HCID 51347784, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. concentrationThe solvent was concentrated
  2. customthe crude product was purified on silica
  3. custom1H 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

Sources & evidence

ORD record
ord-119c71854be24711829c37fabd13d274
Source dataset
uspto-grants-2014_04
Patent number
US08710243B2

Reaction notes

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