N,N-Dimethylaniline → HCID 67757094, compound

HRID 1657222Notes

Reaction equation

HRID 1657222 reaction equation
[NH2:1][C:2]1[C:3]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])=[C:4]2[C:10]3[CH2:11][CH2:12][CH2:13][C:9]=3[S:8][C:5]2=[N:6][CH:7]=1.CN(C)C1C=CC=CC=1.[F:30][C:31]1[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:32]=1[C:33](Cl)=[O:34]>ClCCl>[Cl:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:3]1[C:2]([NH:1][C:33](=[O:34])[C:32]2[CH:36]=[CH:37][C:38]([F:40])=[CH:39][C:31]=2[F:30])=[CH:7][N:6]=[C:5]2[S:8][C:9]3[CH2:13][CH2:12][CH2:11][C:10]=3[C:4]=12

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 5880812,4-Difluorobenzoyl chlorideHCID 19787181HCID 19787181, compound

Product 1

HCID 67757094HCID 67757094, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-amino-4-(2-chlorophenyl)-6,7-dihydro-5H-cyclopenta[1',2':5,4]thieno[2,3-b]pyridine (150 mg) and N,N-dimethylaniline (0.065 ml) in dichloromethane (3 ml) was added dropwise 2,4-difluorobenzoyl chloride (0.07 ml) with ice-cooling. The mixture was stirred for 10 minutes with ice-cooling and then stirred at room temperature for 2 hours. Then, the mixture was washed in turn with water, aqueous saturated NaHCO3 solution and water, and dried over MgSO4. The solvent was distilled off to obtain 4-(2-chlorophenyl)-3-(2,4 -difluorobenzoylamino)-6,7-dihydro-5H-cyclopenta[1',2':5,4]thieno[2,3-b]pyridine (206 mg, 93.6%) as crystals. The crystals were recrystallized from acetone to obtain colorless prisms, mp: 219°-220° C.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringstirred at room temperature for 2 hours
  4. washThen, the mixture was washed in turn with water, aqueous saturated NaHCO3 solution and water
  5. dry with materialdried over MgSO4
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-be6a83bd257f49de9c0fb2e6500ac845
Source dataset
uspto-grants-1993_10
Patent number
US05256782

Reaction notes

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