Water → HCID 66749386, compound

HRID 1405922Notes

Reaction equation

HRID 1405922 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:15]4=[N:16][S:17](=[O:21])(=[O:20])[CH2:18][CH2:19][N:14]4[CH:13]=[CH:12][CH:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].I[CH2:25][CH3:26].O>CN(C=O)C.CCOC(C)=O>[CH2:25]([N:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:15]4=[N:16][S:17](=[O:21])(=[O:20])[CH2:18][CH2:19][N:14]4[CH:13]=[CH:12][CH:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)[CH3:26]

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 66749795HCID 66749795, compound

Product 1

HCID 66749386HCID 66749386, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 9-(1H-indol-5-yl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (131 mg) in DMF (dry) (15 mL) was added NaH (60%, 18.38 mg) at room temperature. The mixture was stirred at the same temperature for 10 min. Iodoethane (0.039 mL) was added and the mixture was stirred at room temperature overnight. Water and EtOAc were added and the extracted organic layer was washed with brine. Silica-gel was added to the organic layer and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (NH-silica gel, eluted with MeOH in EtOAc) to give the title compound (34.6 mg) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. washthe extracted organic layer was washed with brine
  3. additionSilica-gel was added to the organic layer
  4. customthe volatiles were removed in vacuo
  5. customwas purified by column chromatography (NH-silica gel, eluted with MeOH in EtOAc)

Sources & evidence

ORD record
ord-73914f0d86484d22b54b44368c08c606
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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