Cyanamide → HCID 178480751, compound

HRID 522482Notes

Reaction equation

HRID 522482 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[C:10]([O:15][C:16]([F:19])([F:18])[F:17])[CH:9]=2)[CH2:4][CH2:3]1.[N:20]#[C:21][NH2:22]>Cl.O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:21]([NH2:22])=[NH:20])=[C:10]([O:15][C:16]([F:19])([F:17])[F:18])[CH:9]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 9864CyanamideHCID 666783064-(4-Methyl-piperazin-1-yl)-2-trifluoromethoxy-phenylamine

Product 1

HCID 178480751HCID 178480751, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-(4-methyl-piperazin-1-yl)-2-trifluoromethoxy-phenylamine (275 mg, 1 mmol) in HCl 6N (1 mL), cyanamide (336 mg, 8.0 mmol) was added and the reaction was stirred at 60° C. for 1 hours. The mixture was cooled down to room temperature, diluted with H2O (3 mL), extracted with DCM (10 mL). NaOH 2N was added to pH>11. The aqueous phase was extracted with Et2O (3×10 mL), dried over Na2SO4 and concentrated. The residue was crystallized from Et2O to give the title compound (240 mg, 76% yield) as a white solid.

Workup

  1. temperatureThe mixture was cooled down to room temperature
  2. extractionextracted with DCM (10 mL)
  3. additionNaOH 2N was added to pH>11
  4. extractionThe aqueous phase was extracted with Et2O (3×10 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was crystallized from Et2O

Sources & evidence

ORD record
ord-07e2fa86e36e48c88e34929cd427c5b9
Source dataset
uspto-grants-2016_05
Patent number
US09333205B2

Reaction notes

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