Sodium Acetate → HCID 73865445, compound

HRID 1458379Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)=[CH:15][C:14]([C:31](=O)[CH3:32])=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1.C([O-])(=O)C.[Na+].Cl.[O:40]([NH2:42])[CH3:41]>>[CH3:41][O:40][N:42]=[C:31]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[CH:5]=1)=[C:17]2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1)[CH3:32]

Participants

Reactant 3

HCID 517045Sodium Acetate

HCID 521874O-Methylhydroxylamine hydrochloride

HCID 22100898HCID 22100898, compound

Product 1

HCID 73865445HCID 73865445, compoundYield 98.1%

Procedure

To a solution of 1-{2-(3,5-dimethylphenyl)-3-[2-(4-pyridin-4-yl-butylamino)ethyl]-1H-indol-5-yl}ethanone (22 mg in 0.50 mL methanol) was added 102 mg sodium acetate (trihydrate) followed by 63 mg methoxylamine hydrochloride and the mixture stirred at room temperature. After 20 hours, the mixture was concentrated in vacuo and the residue suspended in ethyl acetate, and washed successively with saturated aqueous sodium bicarbonate and brine. The organic portion was dried over sodium sulfate and the concentrate purified by preparative TLC on silica gel (methylene chloride:methanol:ammonium hydroxide, 90:10:0.25) to give the title compound (23 mg). m/e=469 (M+H).

Workup

concentrationthe mixture was concentrated in vacuo
washwashed successively with saturated aqueous sodium bicarbonate and brine
dry with materialThe organic portion was dried over sodium sulfate
customthe concentrate purified by preparative TLC on silica gel (methylene chloride:methanol:ammonium hydroxide, 90:10:0.25)

Sources & evidence

ORD record: ord-8698f1b3f5a44106ae22ac66a21f8729
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05849764

Reaction notes

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