Perchloric Acid → HCID 178489026, compound

HRID 1754064Notes

Reaction equation

HRID 1754064 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[NH2:13][C:14]1[NH:18][N:17]=[CH:16][C:15]=1[C:19]#[N:20].[N:21]#[C-:22].[CH2:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1.Cl(O)(=O)(=O)=O>CO>[CH:23]1([NH:21][C:22]2[N:18]3[N:17]=[CH:16][C:15]([C:19]#[N:20])=[C:14]3[NH:13][C:5]=2[C:4]2[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:3]=2[O:2][CH3:1])[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 24247Perchloric AcidHCID 691752,4-DimethoxybenzaldehydeHCID 855155-Amino-4-cyanopyrazoleHCID 131733666HCID 131733666, compound

Product 1

HCID 178489026HCID 178489026, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a clear light brown solution of 2,4-dimethoxybenzaldehyde (1.0 g, 6.02 mmol) and 5-amino-1H-pyrazole-4-carbonitrile (651 mg, 6.02 mmol) in methanol (21 mL) in a 50 mL sealed tube were added cyclopentane isonitrile (579 mg, 673 μL, 6.02 mmol) and perchloric acid (121 mg, 108 μL, 1.2 mmol) at RT under nitrogen atmosphere. Then, the nitrogen line was disconnected and the flask was sealed with a cap. The resulting dark brown solution slowly became a suspension within 10 minutes which was then stirred for 15 h at room temperature (RT). The off-white solids were collected by filtration and washed with methanol. After air drying, 1.09 g (51.5%) of 3-(cyclopentylamino)-2-(2,4-dimethoxyphenyl)-1H-imidazo[1,2-b]pyrazole-7-carbonitrile was isolated as an off-white solid. LC/MS calcd. for C19H21N5O2 (m/e) 351.408, obsd. 352.2 (M+H, ES+).

Workup

  1. customthe flask was sealed with a cap
  2. customwithin 10 minutes
  3. filtrationThe off-white solids were collected by filtration
  4. washwashed with methanol
  5. customAfter air drying

Sources & evidence

ORD record
ord-c2121f132e8e4bcaa432a1f1afe2dcf2
Source dataset
uspto-grants-2015_10
Patent number
US09169215B2

Reaction notes

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