4-Ethylbenzaldehyde → HCID 178435864, compound

HRID 1754066Notes

Reaction equation

HRID 1754066 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[C:7]#[N:8].[CH2:9]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1)[CH3:10].[CH:19]1([N+:24]#[C-:25])[CH2:23][CH2:22][CH2:21][CH2:20]1.Cl(O)(=O)(=O)=O>CO>[CH:19]1([NH:24][C:25]2[N:6]3[N:5]=[CH:4][C:3]([C:7]#[N:8])=[C:2]3[NH:1][C:15]=2[C:14]2[CH:17]=[CH:18][C:11]([CH2:9][CH3:10])=[CH:12][CH:13]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 208614-EthylbenzaldehydeHCID 24247Perchloric AcidHCID 855155-Amino-4-cyanopyrazoleHCID 2734784Cyclopentyl Isocyanide

Product 1

HCID 178435864HCID 178435864, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a clear colorless solution of 5-amino-1H-pyrazole-4-carbonitrile (161 mg, 1.49 mmol) in methanol (3 mL) were added 4-ethylbenzaldehyde (200 mg, 204 μL, 1.49 mmol) followed by cyclopentyl isonitrile (143 mg, 167 μL, 1.49 mmol) and perchloric acid (29.9 mg, 26.7 μL, 0.298 mmol) at RT under nitrogen atmosphere. The resulting brown solution was stirred for 15 h and during this period (within 5 min) lot of solids were formed. The solids were collected by filtration and washed with methanol. After air drying, 88 mg (18.5% yield) of 3-(cyclopentylamino)-2-(4-ethylphenyl)-1H-imidazo[1,2-b]pyrazole-7-carbonitrile was isolated as an off-white solid. LC/MS calcd. for C19H21N5 (m/e) 319.4, obsd. 320.1 (M+H, ES+).

Workup

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

Sources & evidence

ORD record
ord-a730c9b43681401497a4928a3c1cceae
Source dataset
uspto-grants-2015_10
Patent number
US09169215B2

Reaction notes

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