Perchloric Acid → HCID 178489025, compound

HRID 1754072Notes

Reaction equation

HRID 1754072 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH2:12][C:13]1[NH:17][N:16]=[CH:15][C:14]=1[C:18]#[N:19].[CH:20]1([N+:25]#[C-:26])[CH2:24][CH2:23][CH2:22][CH2:21]1.Cl(O)(=O)(=O)=O>CO>[CH:20]1([NH:25][C:26]2[N:17]3[N:16]=[CH:15][C:14]([C:18]#[N:19])=[C:13]3[NH:12][C:4]=2[C:3]2[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[CH:9][C:2]=2[F:1])[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 24247Perchloric AcidHCID 855155-Amino-4-cyanopyrazoleHCID 2734784Cyclopentyl IsocyanideHCID 27348732-Fluoro-4-methoxybenzaldehyde

Product 1

HCID 178489025HCID 178489025, compoundYield 11.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a clear light yellow solution of 2-fluoro-4-methoxybenzaldehyde (802 mg, 5.2 mmol) and 5-amino-1H-pyrazole-4-carbonitrile (562 mg, 5.2 mmol) in methanol (20 mL) were added a neat cyclopentyl isonitrile (500 mg, 5.2 mmol) and perchloric acid (104 mg, 93.3 μL, 1.04 mmol) at RT under nitrogen atmosphere. Lots of brown solids were precipitated within 1 h and the resulting suspension was stirred for 15 h. After 15 h, it became a dark brown solution without any solids. Then, the solvent was removed under vacuum and the residue was purified using an ISCO (120 g) column chromatography eluting with 0-50% EA in hexanes. The desired fractions were combined and the solvent was removed under vacuum to obtain 203 mg (11.5% yield) of 3-(cyclopentylamino)-2-(2-fluoro-4-methoxyphenyl)-1H-imidazo[1,2-b]pyrazole-7-carbonitrile as an yellow solid. LC/MS calcd. for C18H18FN5O (m/e) 339.37, obsd. 340.2 (M+H, ES+).

Workup

  1. customLots of brown solids were precipitated within 1 h
  2. waitAfter 15 h
  3. customThen, the solvent was removed under vacuum
  4. customthe residue was purified
  5. washeluting with 0-50% EA in hexanes
  6. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-044ecf6da0e9441d9b70b4a5e0929189
Source dataset
uspto-grants-2015_10
Patent number
US09169215B2

Reaction notes

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