Dimethylformamide → HCID 87576195, compound

HRID 2111431Notes

Reaction equation

HRID 2111431 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[NH:14][C:13](=[O:15])[CH:12]3[CH:8]([CH2:9][CH2:10][CH2:11]3)[N:7]([CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[C:6]=2[N:21]=1.[CH3:22]N(C)C=O.C(=O)([O-])[O-].[Cs+].[Cs+].IC>C(OCC)(=O)C.O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:14]([CH3:22])[C:13](=[O:15])[CH:12]3[CH:8]([CH2:9][CH2:10][CH2:11]3)[N:7]([CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[C:6]=2[N:21]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 87577134HCID 87577134, compound

Product 1

HCID 87576195HCID 87576195, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 0.68 g (0.0022 mole) of (rac)-6-chloro-4-cyclopentyl-2,3,3a,4,9,10a-hexahydro-1H-4,5,7,9-tetraaza-benzo[f]azulen-10-one (VI-68), 20 mL of dimethylformamide and 1.83 g (0.0056 mole) of cesium carbonate was added 1.254 g (0.0088 mole) of iodomethane. The mixture was stirred for 20 minutes, then diluted with ethyl acetate and water. The water layer was extracted twice with ethyl acetate and the combined ethyl acetate layers washed successively with water, then brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 0.580 g of (rac)-6-chloro-4-cyclopentyl-9-methyl-2,3,3a,4,9,10a-hexahydro-1H-4,5,7,9-tetraazabenzo[f]azulen-10-one (VII-68), which was used in the next step without further purification.

Workup

  1. extractionThe water layer was extracted twice with ethyl acetate
  2. washthe combined ethyl acetate layers washed successively with water
  3. dry with materialbrine, dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-efe5a3dbbf8f42418d3629eafb09cfc7
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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