Water → HCID 22141177, compound

HRID 1826392Notes

Reaction equation

HRID 1826392 reaction equation
[CH3:1][C:2]1([C:17]2[CH:18]=[C:19]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=2)[CH:7]2[CH:3]1[CH2:4][N:5]([C:8](=O)/[CH:9]=[CH:10]/[C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)[CH2:6]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C(OCC)(=O)C>[NH3:5].[CH3:1][C:2]1([C:17]2[CH:18]=[C:19]([NH:23][S:24]([CH3:27])(=[O:25])=[O:26])[CH:20]=[CH:21][CH:22]=2)[CH:7]2[CH:3]1[CH2:4][N:5]([CH2:8]/[CH:9]=[CH:10]/[C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)[CH2:6]2

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 21226445Aluminium lithium hydrideHCID 22141136HCID 22141136, compound

Product 2

HCID 222AmmoniaHCID 22141177HCID 22141177, compoundYield 139.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(3-{6-methyl-3-[(E)-3-(2-thienyl)-2-propenoyl]-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide (Preparation 133, 100 mg, 0.248 mmol) in anhydrous tetrahydrofuran (2.5 ml) under a nitrogen atmosphere at 0° C. was added dropwise lithium aluminium hydride (1.0M solution in tetrahydrofuran, 0.25 ml, 0.25 mmol) and the reaction mixture was stirred at room temperature for 7 h. The rapidly stirred reaction mixture was treated sequentially with water (0.25 ml), sodium carbonate (250 mg) and ethyl acetate (2.5 ml). The reaction mixture was left to stir overnight and then was filtered and concentrated in vacuo. This was purified by chromatography using silica gel (2 g) eluting with ethyl acetate:hexane:0.880 ammonia (60:40:1) to afford the title compound as a pale yellow oil (67 mg, 69%).

Workup

  1. customThe rapidly stirred reaction mixture
  2. waitThe reaction mixture was left
  3. stirringto stir overnight
  4. filtrationwas filtered
  5. concentrationconcentrated in vacuo
  6. customThis was purified by chromatography
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-beb5a6a07ab9496daec901fce8686293
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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