Perchloric Acid → HCID 178493377, compound

HRID 1754081Notes

Reaction equation

HRID 1754081 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[C:7]#[N:8].[CH2:9]([O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[C:19]([O:25][CH3:26])[CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH:27]1([N+:32]#[C-:33])[CH2:31][CH2:30][CH2:29][CH2:28]1.Cl(O)(=O)(=O)=O>CO>[CH2:9]([O:16][C:17]1[CH:24]=[CH:23][C:20]([C:21]2[NH:1][C:2]3[N:6]([C:33]=2[NH:32][CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)[N:5]=[CH:4][C:3]=3[C:7]#[N:8])=[C:19]([O:25][CH3:26])[CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 24247Perchloric AcidHCID 855155-Amino-4-cyanopyrazoleHCID 2734784Cyclopentyl IsocyanideHCID 42939904-Benzyloxy-2-methoxybenzaldehyde

Product 1

HCID 178493377HCID 178493377, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 5-amino-1H-pyrazole-4-carbonitrile (193 mg, 1.79 mmol) and 4-(benzyloxy)-2-methoxybenzaldehyde (433 mg, 1.79 mmol) in a vial under nitrogen atmosphere were added methanol (10 mL) followed by cyclopentyl isonitrile (172 mg, 200 μL, 1.79 mmol) and perchloric acid (35.9 mg, 32.1 μL, 0.358 mmol) at RT. Then, the resulting brown solution was stirred for 15 h by which time lot of solids precipitated. These solids were collected by filtration and washed with methanol. After air drying, 320 mg of (42%) 2-(4-benzyloxy-2-methoxyphenyl)-3-(cyclopentylamino)-1H-imidazo[1,2-b]pyrazole-7-carbonitrile, the desired product was isolated as a white solid. LC/MS calcd. for C25H25N5O2 (m/e) 427.5, obsd. 428.1 (M+H, ES+).

Workup

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

Sources & evidence

ORD record
ord-d51cbf9b2a254681b100403b4a42262b
Source dataset
uspto-grants-2015_10
Patent number
US09169215B2

Reaction notes

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