Perchloric Acid → HCID 178489027, compound

HRID 1754079Notes

Reaction equation

HRID 1754079 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[C:7]#[N:8].[CH3:9][O:10][C:11]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:12]=1[CH:13]=O.[CH:21]1([N+:27]#[C-:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.Cl(O)(=O)(=O)=O>CO>[CH:21]1([NH:27][C:28]2[N:6]3[N:5]=[CH:4][C:3]([C:7]#[N:8])=[C:2]3[NH:1][C:13]=2[C:12]2[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[CH:18][C:11]=2[O:10][CH3:9])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 24247Perchloric AcidHCID 691752,4-DimethoxybenzaldehydeHCID 79129Cyclohexyl isocyanideHCID 855155-Amino-4-cyanopyrazole

Product 1

HCID 178489027HCID 178489027, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 5-amino-1H-pyrazole-4-carbonitrile (491 mg, 4.54 mmol) and 2,4-dimethoxybenzaldehyde (754 mg, 4.54 mmol) in a vial under nitrogen atmosphere were added methanol (20 mL) followed by cyclohexyl isonitrile (500 mg, 581 μL, 4.54 mmol) and perchloric acid (91.2 mg, 81.4 μL, 0.908 mmol) at RT. Then, the resulting brown solution was stirred for 15 h by which time lots of solid was formed. These solids were collected by filtration and washed with methanol. After air drying, 495 mg (30% yield) of 3-(cyclohexylamino)-2-(2,4-dimethoxyphenyl)-1H-imidazo[1,2-b]pyrazole-7-carbonitrile was isolated as a white solid. LC/MS calcd. for C20H23N5O2 (m/e) 365.43, obsd. 366.0 (M+H, ES+).

Workup

  1. customwas formed
  2. filtrationThese solids were collected by filtration
  3. washwashed with methanol
  4. customAfter air drying

Sources & evidence

ORD record
ord-62951ebaca03410bb9e7ac52534dea0c
Source dataset
uspto-grants-2015_10
Patent number
US09169215B2

Reaction notes

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