O-Methylhydroxylamine hydrochloride → HCID 178448679, compound

HRID 2235434Notes

Reaction equation

HRID 2235434 reaction equation
[CH3:1][C:2]1([CH3:29])[C:10]2[CH:9]=[C:8]3[N:11]=[C:12]([NH:14][C:15](=[O:22])[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[NH:13][C:7]3=[CH:6][C:5]=2[N:4]([CH2:23][C:24](=O)[CH2:25][CH3:26])[C:3]1=[O:28].Cl.[CH3:31][O:32][NH2:33]>CO>[CH3:31][O:32]/[N:33]=[C:24](/[CH2:25][CH3:26])\[CH2:23][N:4]1[C:5]2[CH:6]=[C:7]3[NH:13][C:12]([NH:14][C:15](=[O:22])[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)=[N:11][C:8]3=[CH:9][C:10]=2[C:2]([CH3:1])([CH3:29])[C:3]1=[O:28]

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 178459291HCID 178459291, compound

Product 1

HCID 178448679HCID 178448679, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[7,7-dimethyl-6-oxo-5-(2-oxo-butyl)-3,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl]-benzamide (80 mg) in MeOH (20 ml) is added O-methyl-hydroxylamine hydrochloride (20.5 mg; 0.25 mmol) and the mixture is stirred at RT for 18 h. After evaporation EtOAc is added and the organic phase is washed three times with saturated K2CO3 solution, dried over MgSO4 and evaporated again. The residue is purified by RP-MPLC eluted with MeCN/water to yield the desired compound (57 mg).

Workup

  1. customAfter evaporation EtOAc
  2. additionis added
  3. washthe organic phase is washed three times with saturated K2CO3 solution
  4. dry with materialdried over MgSO4
  5. customevaporated again
  6. customThe residue is purified by RP-MPLC
  7. washeluted with MeCN/water

Sources & evidence

ORD record
ord-16df45b721f14ec59aa7b35a0c23afba
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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