1,2-Dichloroethane → HCID 178447333, compound

HRID 1258750Notes

Reaction equation

HRID 1258750 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[O:18][C:19]([F:22])([F:21])[F:20])[CH2:7][NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[C:2]=S.[NH2:23][C:24]1[C:31]([NH2:32])=[CH:30][C:27]([C:28]#[N:29])=[C:26]([N:33]2[CH2:38][CH2:37][CH2:36][CH:35]([C:39]([F:42])([F:41])[F:40])[CH2:34]2)[CH:25]=1.CN(C=O)C.C(Cl)CCl>C(Cl)(Cl)Cl.O>[C:28]([C:27]1[C:26]([N:33]2[CH2:38][CH2:37][CH2:36][CH:35]([C:39]([F:42])([F:40])[F:41])[CH2:34]2)=[CH:25][C:24]2[NH:23][C:2]([NH:1][C:4]3[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=3[O:18][C:19]([F:22])([F:21])[F:20])[CH2:7][NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[N:32][C:31]=2[CH:30]=1)#[N:29]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 679577914,5-Diamino-2-(3-trifluoromethyl-piperidin-1-yl)benzonitrileHCID 86674354N-(3-Isothiocyanato-4-trifluoromethoxy-benzyl)-2,2-dimethyl-propionamide

Product 1

HCID 178447333HCID 178447333, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A mixture of N-(3-isothiocyanato-4-trifluoromethoxy-benzyl)-2,2-dimethyl-propionamide (135 mg, 0.406 mmol), 4,5-diamino-2-(3-trifluoromethyl-piperidin-1-yl)benzonitrile (115 mg, 0.406 mmol) and DMF (2 mL) was stirred at rt for 4 h. EDC (101 mg, 0.527 mmol) was added and mixture was stirred at rt overnight. The mixture was treated with water and extracted with Et2O. Concentration and purification by column chromatography gave an oil. The oil was treated with CHCl3 and the precipitate was collected by filtration.

Workup

  1. stirringmixture was stirred at rt overnight
  2. extractionextracted with Et2O
  3. concentrationConcentration and purification by column chromatography
  4. customgave an oil
  5. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-1ca4f1d92d9d43c5be95592e6fc7dbab
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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