Hydroxyamine hydrochloride → HCID 72629051, compound

HRID 968258Notes

Reaction equation

HRID 968258 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16](=O)[C:17]([NH:19][C:20]3[S:24][N:23]=[C:22]([CH3:25])[CH:21]=3)=[O:18])=[CH:8]2)=[CH:4][CH:3]=1.Cl.[NH2:30][OH:31].C([O-])(=O)C.[Na+]>CCO.C1COCC1>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16](=[N:30][OH:31])[C:17]([NH:19][C:20]3[S:24][N:23]=[C:22]([CH3:25])[CH:21]=3)=[O:18])=[CH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 10158451HCID 10158451, compound

Product 1

HCID 72629051HCID 72629051, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of 2-[1-(4-chlorobenzyl)-1H-indol-3-yl]-N-(3-methyl-isothiazol-5-yl)-2-oxo-acetamide (0.102 g, 0.25 mmol), hydroxylamine hydrochloride (17 mg, 0.25 mmol), and sodium acetate (0.1 g, 1.2 mmol) in EtOH (3 mL) and THF (3 mL) was heated to reflux for 3 days. After being cooled to rt, the reaction mixture was poured into ice-H2O (20 mL). The precipitated product 2-[1-(4-Chloro-benzyl)-1H-indol-3-yl]-2-hydroxyimino-N-(3-methyl-isothiazol-5-yl)-acetamide was collected by filtration, washed with H2O, and dried in vacuo (95 mg, 90%). 1H NMR (DMSO-d6) δ 2.3 (s, 3H), 5.6 (s, 2H), 6.9 (s, 1H), 7.0-7.5 (m, 7H), 8.1 (d, 1H, J=7), 8.65 (s, 1H). ESMS calcd for (C21H17ClN4O2S): 424.1; found 425.1 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 days
  3. filtrationThe precipitated product 2-[1-(4-Chloro-benzyl)-1H-indol-3-yl]-2-hydroxyimino-N-(3-methyl-isothiazol-5-yl)-acetamide was collected by filtration
  4. washwashed with H2O
  5. customdried in vacuo (95 mg, 90%)

Sources & evidence

ORD record
ord-ff8cda1dd2e04296b147ba0b9f9a27f5
Source dataset
uspto-grants-2005_10
Patent number
US06958348B2

Reaction notes

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