Sodium Bicarbonate → N-(2-(3-benzyl-2-(3,3-dimethylazetidin-1-yl)-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide

HRID 587890Notes

Reaction equation

HRID 587890 reaction equation
[CH2:1]([CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:18][CH2:19][NH:20][S:21]([C:24]3[N:25]=[CH:26][N:27]([CH3:29])[CH:28]=3)(=[O:23])=[O:22])[CH:15]=2)[CH2:10][CH:9]1[NH:30][CH2:31][C:32]([CH3:36])([CH3:35])[CH2:33]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+]>C(#N)C.ClCCl>[CH2:1]([CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:18][CH2:19][NH:20][S:21]([C:24]3[N:25]=[CH:26][N:27]([CH3:29])[CH:28]=3)(=[O:23])=[O:22])[CH:15]=2)[CH2:10][CH:9]1[N:30]1[CH2:33][C:32]([CH3:36])([CH3:35])[CH2:31]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 66741593N-(2-(3-benzyl-2-(3-chloro-2,2-dimethylpropylamino)-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide

Product 1

HCID 56837060N-(2-(3-benzyl-2-(3,3-dimethylazetidin-1-yl)-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Dissolved N-(2-(3-benzyl-2-(3-chloro-2,2-dimethylpropylamino)-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide (17.7 mg, 0.033 mmol in dry acetonitrile (2.000 ml) and added sodium bicarbonate (5.60 mg, 0.067 mmol). Microwave at 70° C. for 2 h. Evaporated solvents and re-dissolved in dichloromethane, washed with water and brine, dried over magnesium sulfate, filtered and evaporated to obtain the crude product as clear white oil, that was purified by column chromatography on 1.5×2.5 cm SiO2 using 5% methanol in dichloromethane to afford N-(2-(3-benzyl-2-(3,3-dimethylazetidin-1-yl)-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide as a white solid. m=1.7 mg (10%)

Workup

  1. washwashed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto obtain the crude product as clear white oil, that
  6. customwas purified by column chromatography on 1.5×2.5 cm SiO2 using 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-39f87b940a1c4630b7669c46e8094049
Source dataset
uspto-grants-2016_01
Patent number
US09227930B2

Reaction notes

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