Perchloric Acid → HCID 178510453, compound

HRID 1754068Notes

Reaction equation

HRID 1754068 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[NH2:10][C:11]1[NH:15][N:14]=[CH:13][C:12]=1[C:16]#[N:17].[N:18]#[C-:19].[CH2:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1.Cl(O)(=O)(=O)=O>CO>[CH:20]1([NH:18][C:19]2[N:15]3[N:14]=[CH:13][C:12]([C:16]#[N:17])=[C:11]3[NH:10][C:6]=2[C:5]2[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=2)[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 24247Perchloric AcidHCID 707414-BromobenzaldehydeHCID 855155-Amino-4-cyanopyrazoleHCID 131733666HCID 131733666, compound

Product 1

HCID 178510453HCID 178510453, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a clear colorless solution of 4-bromobenzaldehyde (3.71 g, 20.1 mmol) and 5-amino-1H-pyrazole-4-carbonitrile (2.17 g, 20.1 mmol) in a 350 mL sealed tube in methanol (70 mL) were added cyclopentane isonitrile (1.93 g, 2.24 mL, 20.1 mmol) and perchloric acid (403 mg, 360 μL, 4.01 mmol) at RT under nitrogen atmosphere. Then, the nitrogen line was disconnected and the flask was sealed with a cap. The resulting light yellow solution slowly became a suspension within 5 minutes which was then stirred for 15 h at RT. The off-white solids were collected by filtration and washed with methanol. After air drying, 5.1 g (68.7% yield) of 3-(cyclopentylamino)-2-(4-bromophenyl)-1H-imidazo[1,2-b]pyrazole-7-carbonitrile was isolated as an off-white solid. LC/MS calcd. for C17H16BrN5 (m/e) 370.25, obsd. 372.0 (M+H, ES+).

Workup

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

Sources & evidence

ORD record
ord-bb4df33ebb824178be38f108a5937af9
Source dataset
uspto-grants-2015_10
Patent number
US09169215B2

Reaction notes

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