Hydrochloric Acid → HCID 86724090, compound

HRID 1748748Notes

Reaction equation

HRID 1748748 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[S:15][C:14]([CH3:17])([CH3:16])[CH2:13][NH:12][C:11]2[N:18]([CH3:22])[N:19]=[C:20]([CH3:21])[C:10]1=2.[H-].[Na+].CI.[C:27](=O)(O)[O-].[Na+].Cl>CN(C=O)C.C(OCC)(=O)C.C(Cl)Cl.C(OCC)(=O)C>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[S:15][C:14]([CH3:17])([CH3:16])[CH2:13][N:12]([CH3:27])[C:11]2[N:18]([CH3:22])[N:19]=[C:20]([CH3:21])[C:10]1=2

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 136216145HCID 136216145, compound

Product 1

HCID 86724090HCID 86724090, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

To 4-(2,4-dichlorophenyl)-1,3,6,6-tetramethyl-7,8-dihydro-4H-pyrazolo[3,4-e][1,4]thiazepine (0.12 g, 0.33 mmol, Example #D.4) dissolved in DMF (10 mL), was added NaH (0.133 g, 3.33 mmol, 60% dispersion in mineral oil) and methyl iodide (0.21 mL, 3.33 mmol). The reaction mixture was stirred for about 24 h at rt. To the reaction mixture was added 5% aqueous sodium bicarbonate (30 mL) and ethyl acetate (25 mL). The layers were separated and the organic layer was washed with water (25 mL), dried (MgSO4), filtered and concentrated in vacuo. The resulting residue was purified by column chromatography (SiO2, ethyl acetate/DCM (1:9 followed by 1:4)), to 4-(2,4-dichlorophenyl)-1,3,6,6,8-pentamethyl-4,7-dihydropyrazolo[3,4-e]thiazepine (0.07 g, 0.189 mmol, 57%), which was dissolved in ethyl acetate and converted into the HCl salt (using 1M HCl/ethanol). The precipitated solid is collected by filtration and washed with a small amount of diethyl ether to afford 4-(2,4-dichlorophenyl)-1,3,6,6,8-pentamethyl-4,7-dihydropyrazolo[3,4-e][1,4]thiazepine hydrochloride (0.053 g, 0.13 mmol, 39%) as an off white solid. LC-MS (Table 1, Method d) Rr=3.05 min, m/z 370 (M+H)+

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with water (25 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. filtrationThe precipitated solid is collected by filtration
  7. washwashed with a small amount of diethyl ether

Sources & evidence

ORD record
ord-4083d2593d7f46aaa022b9ec5765f66a
Source dataset
uspto-grants-2015_10
Patent number
US09150592B2

Reaction notes

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