2-Methoxyethanol → HCID 57642342, compound

HRID 2112508Notes

Reaction equation

HRID 2112508 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([F:20])[C:17](F)=[CH:18][C:13]=2[NH:12][C:11](=[S:21])[CH2:10][N:9]=1.[H-].[Na+].[CH3:24][O:25][CH2:26][CH2:27][OH:28]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([F:20])[C:17]([O:28][CH2:27][CH2:26][O:25][CH3:24])=[CH:18][C:13]=2[NH:12][C:11](=[S:21])[CH2:10][N:9]=1

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 57642320HCID 57642320, compound

Product 1

HCID 57642342HCID 57642342, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1.0 g (0.0031 mole) of 5-(2-chlorophenyl)-1,3-dihydro-7,8-difluoro-2H-1,4-benzodiazepin-2-thione (IImm), 0.372 g of sodium hydride and 20 mL of 2-methoxyethanol was heated in a microwave vessel at 120° C. for 30 minutes, cooled and then diluted with ethyl acetate. The mixture was washed successively with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was triturated with ethyl acetate to give 0.74 g of 5-(2-chlorophenyl)-1,3-dihydro-7-fluoro-8-methoxyethoxy-2H-1,4-benzodiazepin-2-thione (IIf) as a white solid, which was then used to prepare 5-(2-chlorophenyl)-1,2-dihydro-7-fluoro-8-methoxyethoxy-3-methyl-pyrazolo[3,4-b][1,4]benzodiazepine (IVf) in accordance with Example 58 without further purification.

Workup

  1. temperaturecooled
  2. washThe mixture was washed successively with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-7d65573e1feb48d181938a400b83d66b
Source dataset
uspto-grants-2009_04
Patent number
US07524840B2

Reaction notes

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