Water → HCID 25056824, compound

HRID 2423121Notes

Reaction equation

HRID 2423121 reaction equation
[H-].[Na+].[CH3:3][N:4]1[CH2:17][C:9]2=[C:10]3[C:14](=[CH:15][CH:16]=[C:8]2[O:7][CH2:6][CH2:5]1)[NH:13][CH:12]=[CH:11]3.[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26](Cl)(=[O:28])=[O:27])#[N:19].O>CN(C=O)C>[CH3:3][N:4]1[CH2:17][C:9]2=[C:10]3[C:14](=[CH:15][CH:16]=[C:8]2[O:7][CH2:6][CH2:5]1)[N:13]([S:26]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:18]#[N:19])(=[O:28])=[O:27])[CH:12]=[CH:11]3

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5223472-Cyanobenzenesulfonyl ChlorideHCID 672416342-Methyl-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole2×

Product 1

HCID 25056824HCID 25056824, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60% in mineral oil, 0.040 g, 1.0 mmol) was charged into a pyrex tube under nitrogen gas and 2-methyl-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole (Intermediate 6, 100 mg, 0.492 mmol) in dry DMF (1 mL) was added. The reaction mixture was stirred at room temperature for 20 minutes before 2-cyanobenzenesulfonyl chloride (0.11 g, 0.50 mmol) was added and the reaction mixture was stirred for 1 hour. Water (2 mL) was added and the solution was extracted with DCM. The combined organics were evaporated and the solid residue was washed with diethyl ether to give 64 mg of the title compound. MS m/z 368 [M+H]+.

Workup

  1. additionwas added
  2. extractionthe solution was extracted with DCM
  3. customThe combined organics were evaporated
  4. washthe solid residue was washed with diethyl ether

Sources & evidence

ORD record
ord-722799d606b145339b20eacefc8d922e
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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