Water → HCID 86689313, compound

HRID 1852498Notes

Reaction equation

HRID 1852498 reaction equation
[Na].[NH:2]1[C:6]([C:7]2[CH:8]=[C:9]([N:13]3[C:19](=[O:20])[CH2:18][C:17](=[O:21])[NH:16][C:15]4[C:22]5[CH2:23][CH2:24][CH2:25][C:26]=5[CH:27]=[CH:28][C:14]3=4)[CH:10]=[CH:11][CH:12]=2)=[N:5][N:4]=[N:3]1.[CH3:29]I.O>CS(C)=O>[CH3:29][N:4]1[N:3]=[N:2][C:6]([C:7]2[CH:8]=[C:9]([N:13]3[C:19](=[O:20])[CH2:18][C:17](=[O:21])[NH:16][C:15]4[C:22]5[CH2:23][CH2:24][CH2:25][C:26]=5[CH:27]=[CH:28][C:14]3=4)[CH:10]=[CH:11][CH:12]=2)=[N:5]1.[CH3:29][N:5]1[C:6]([C:7]2[CH:8]=[C:9]([N:13]3[C:19](=[O:20])[CH2:18][C:17](=[O:21])[NH:16][C:15]4[C:22]5[CH2:23][CH2:24][CH2:25][C:26]=5[CH:27]=[CH:28][C:14]3=4)[CH:10]=[CH:11][CH:12]=2)=[N:2][N:3]=[N:4]1

Participants

6

Reactant 3

HCID 962WaterHCID 6328Methyl iodideHCID 178516630HCID 178516630, compound

Product 2

HCID 86689313HCID 86689313, compoundYield 38%HCID 86689314HCID 86689314, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-[3-(1H-Tetrazol-5-yl)phenyl]-5,8,9,10-tetrahydroindeno[5,4-b][1,4]diazepine-2,4(1H,3H)-dione sodium salt (46 mg, 0.12 mmol) was dissolved in dry dimethylsulfoxide (2 mL). To the solution was added methyl iodide (37 μL, 0.60 mmol). The mixture was stirred at room temperature for 72 hours. To the mixture was added water. The mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/1-3/1) to give 5-[3-(2-methyl-2H-tetrazol-5-yl)phenyl]-5,8,9,10-tetrahydroindeno[5,4-b][1,4]diazepine-2,4(1H,3H)-dione (17 mg, yield 38%) and 5-[3-(1-methyl-1H-tetrazol-5-yl)phenyl]-5,8,9,10-tetrahydroindeno[5,4-b][1,4]diazepine-2,4(1H,3H)-dione (5 mg, yield 11%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed by evaporation under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/1-3/1)

Sources & evidence

ORD record
ord-6311dc8a5a6c40749e96b50301a8b33e
Source dataset
uspto-grants-2015_02
Patent number
US08962613B2

Reaction notes

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