Ethyl isocyanate → HCID 135875704, compound

HRID 1034952

Reaction equation

HRID 1034952 reaction equation
[C:1]1([C:7]2[C:11]([CH3:12])=[N:10][N:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8]=2[NH2:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.C(N=[C:23]=[O:24])C>N1C=CC=CC=1>[CH3:12][C:11]1[C:7]2[C:1]3[CH2:6][CH2:5][CH2:4][CH2:3][C:2]=3[C:23](=[O:24])[NH:19][C:8]=2[N:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:10]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 694762524-cyclohex-1-enyl-5-methyl-2-phenyl-2H-pyrazol-3-ylamine

Product 1

HCID 135875704HCID 135875704, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of EXAMPLE 7A (1.26 g, 5 mmol) in pyridine (10 mL) was added ethyl isocyanate (1.18 mL, 15 mmol). The solution was heated at reflux for 7 hours, cooled, concentrated and the residue triturated with methanol. The solid was collected by filtration, washed with methanol and dried to give 493 mg (35%) of the title compound. 1H NMR (DMSO-d6) 1.72-1.83 (m, 4H), 2.49-2.55 (m, 2H), 2.57 (s, 3H), 3.05 (t, J=5.2 Hz, 2H), 7.24 (t, J=7.4 Hz, 1H), 7.43-7.53 (m, 2H), 8.19 (d, J=7.7 Hz, 2H), 11.27 (br s, 1H).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 7 hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. customthe residue triturated with methanol
  6. filtrationThe solid was collected by filtration
  7. washwashed with methanol
  8. customdried

Sources & evidence

ORD record
ord-3de6d01863ce43f0ae031c3f79e6f5a4
Source dataset
uspto-grants-2013_10
Patent number
US08546368B2

Linked notes

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