Sodium hydride → HCID 20434945, compound

HRID 1154312Notes

Reaction equation

HRID 1154312 reaction equation
[H-].[Na+].[S:3]1(=[O:10])(=[O:9])[N:8]=[CH:7][CH:6]=[CH:5][NH:4]1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[N:19]=[CH:18][N:17]=[C:16]2[N:25]1[CH2:30][CH2:29][CH:28]([CH2:31]I)[CH2:27][CH2:26]1>CN(C)C=O>[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[N:19]=[CH:18][N:17]=[C:16]2[N:25]1[CH2:30][CH2:29][CH:28]([CH2:31][N:8]2[CH:7]=[CH:6][CH:5]=[N:4][S:3]2(=[O:10])=[O:9])[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 156326991lambda~6~,2,6-Thiadiazine-1,1(2H)-dioneHCID 204349324-[4-(Iodomethyl)piperidin-1-yl]-6,7-dimethoxyquinazoline

Product 1

HCID 20434945HCID 20434945, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.20 g. of a 50% dispersion in oil) was added to a stirred solution of 2H-1,2,6-thiadiazine-1,1-dioxide (0.56 g) in dimethylformamide (4 cm3). After 0.5 hours 1-(6,7-dimethoxyquinazolin-4-yl)-4-iodomethylpiperidine (0.70 g) was added and the mixture was warmed at 70° for 10 hours. The solvent was removed in vacuo, water was added and the mixture was extracted with chloroform (4×20 cm3). The dried (MgSO4) extracts were evaporated and the residue was chromatographed on silica (MK 60.9385) eluting with methanol:ethyl acetate, 1:19, to give a foam. Crystallisation from ethyl acetate afforded 1-(6,7-dimethoxyquinazolin-4-yl)-4-(1,1-dioxo-1,2,6-thiadiazin-2-yl)methyl piperidine as white microcrystals, m.p. 173°-174°, (0.27 g).

Workup

  1. temperaturethe mixture was warmed at 70° for 10 hours
  2. customThe solvent was removed in vacuo, water
  3. additionwas added
  4. extractionthe mixture was extracted with chloroform (4×20 cm3)
  5. dry with materialThe dried (MgSO4) extracts
  6. customwere evaporated
  7. customthe residue was chromatographed on silica (MK 60.9385)
  8. washeluting with methanol
  9. customethyl acetate, 1:19, to give a foam
  10. customCrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-fc5803bb9001442eb23df7c6aa1a4f90
Source dataset
uspto-grants-1984_12
Patent number
US04489075

Reaction notes

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