Water → HCID 66740676, compound

HRID 587883Notes

Reaction equation

HRID 587883 reaction equation
[CH2:1]([C@@H:8]1[C:16]2[C:11](=[CH:12][C:13]([F:30])=[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][C@@H:9]1[NH:31][C:32](=O)OCC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[K+].O>O1CCCC1>[CH2:1]([C@H:8]1[C:16]2[C:11](=[CH:12][C:13]([F:30])=[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][C@H:9]1[NH:31][CH3:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66741454HCID 66741454, compound

Product 1

HCID 66740676HCID 66740676, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To ethyl cis-1-benzyl-5-fluoro-6-(2-(1-methyl-1H-imidazole-4-sulfonamido)ethoxy)-2,3-dihydro-1H-inden-2-ylcarbamate (45.3 mg, 0.088 mmol) in tetrahydrofuran (1 ml) was added lithium aluminium hydride 1M in tetrahydrofuran (0.263 ml, 0.263 mmol) and the reaction mixture was refluxed for 2 h. Cooled down to room temperature and added a mixture of 0.5N potassium hydroxide (1 ml) and water (7 ml), filtered over Celite, washed with tetrahydrofuran and the Celite Filter cake was poured into tetrahydrofuran, refluxed for 30 min, and again filtered over Celite. The combined organic layers were evaporated, re-dissolved in dichloromethane, washed with sodium bicarbonate and brine, dried over magnesium sulfate, filtered and evaporated to obtain a pale yellow oil, that was purified by flash silica gel chromatography on 4 g SiO2-cartridge using 10% methanol in dichloromethane to obtain cis-N-(2-(3-benzyl-6-fluoro-2-(methylamino)-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide as a pale yellow oil. m=14.2 mg (35%)

Workup

  1. temperaturethe reaction mixture was refluxed for 2 h
  2. additionadded
  3. filtrationfiltered over Celite
  4. washwashed with tetrahydrofuran
  5. filtrationthe Celite Filter cake
  6. additionwas poured into tetrahydrofuran
  7. temperaturerefluxed for 30 min
  8. filtrationagain filtered over Celite
  9. customThe combined organic layers were evaporated
  10. dissolutionre-dissolved in dichloromethane
  11. washwashed with sodium bicarbonate and brine
  12. dry with materialdried over magnesium sulfate
  13. filtrationfiltered
  14. customevaporated
  15. customto obtain a pale yellow oil, that
  16. customwas purified by flash silica gel chromatography on 4 g SiO2-cartridge

Sources & evidence

ORD record
ord-19f9eacf530946dabd3e2796d07f15fb
Source dataset
uspto-grants-2016_01
Patent number
US09227930B2

Reaction notes

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