1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68683028, compound

HRID 1713736Notes

Reaction equation

HRID 1713736 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([F:9])[C:6]([Br:10])=[CH:5][C:3]=1[NH2:4].[C:11](N1C=CN=C1)(N1C=CN=C1)=S.[NH:23]([C:25](=[O:41])[C:26]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)=[CH:31][CH:30]=1)=[O:27])[NH2:24].CCN=C=NCCCN(C)C>CN(C=O)C.O>[Br:10][C:6]1[C:7]([F:9])=[CH:8][C:2]([F:1])=[C:3]([NH:4][C:11]2[O:41][C:25]([C:26]([NH:28][C:29]3[CH:30]=[CH:31][C:32]([N:35]4[CH2:36][CH2:37][O:38][CH2:39][CH2:40]4)=[CH:33][CH:34]=3)=[O:27])=[N:23][N:24]=2)[CH:5]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 802641,1'-ThiocarbonyldiimidazoleHCID 27832955-Bromo-2,4-difluoroanilineHCID 59464167HCID 59464167, compound2×

Product 1

HCID 68683028HCID 68683028, compoundYield 35.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2,4-Difluoro-5-bromoaniline (208 mg, 1.04 mmol) was added to a solution of thiocarbonyldiimidazole (185 mg 1.04 mmol) in DMF (10 mL) and the mixture was stirred for 16 h. 2-Hydrazino-N-(4-morpholin-4-ylphenyl)-2 oxoacetamide (Intermediate 27, 211 mg, 0.8 mmol) was added and the mixture was stirred at 80° C. until a clear solution was obtained. EDAC (306 mg, 1.6 mmol) was added and stirring was continued for a further 1 h. The mixture was cooled then diluted with water (25 mL) and the resulting precipitate was filtered and dried to give the title compound the title compound (135 mg) as a solid;

Workup

  1. stirringthe mixture was stirred at 80° C. until a clear solution
  2. customwas obtained
  3. stirringstirring
  4. waitwas continued for a further 1 h
  5. temperatureThe mixture was cooled
  6. filtrationthe resulting precipitate was filtered
  7. customdried

Sources & evidence

ORD record
ord-3938b4cd1e0847509395706eec5d7c08
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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