Perchloric Acid → HCID 178486592, compound

HRID 1754076Notes

Reaction equation

HRID 1754076 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH:13]=O)=[CH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.[NH2:15][C:16]1[NH:20][N:19]=[CH:18][C:17]=1[C:21]#[N:22].[CH:23]1([N+:28]#[C-:29])[CH2:27][CH2:26][CH2:25][CH2:24]1.Cl(O)(=O)(=O)=O>CO.C(OCC)C>[CH:23]1([NH:28][C:29]2[N:20]3[N:19]=[CH:18][C:17]([C:21]#[N:22])=[C:16]3[NH:15][C:13]=2[C:4]2[C:3]([O:2][CH3:1])=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=2)[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 24247Perchloric AcidHCID 855155-Amino-4-cyanopyrazoleHCID 2734784Cyclopentyl IsocyanideHCID 113213743-METHOXY-2-NAPHTHALDEHYDE

Product 1

HCID 178486592HCID 178486592, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a clear solution of 3-methoxy-2-naphthaldehyde (484 mg, 2.6 mmol) and 5-amino-1H-pyrazole-4-carbonitrile (281 mg, 2.6 mmol) in methanol (5 mL) were added cyclopentyl isonitrile (250 mg, 291 μL, 2.6 mmol) followed by perchloric acid (26.1 mg, 23.3 μL, 260 μmol) at RT under nitrogen atmosphere. The resulting dark brown solution was stirred for 15 h at RT by which time LC/MS analysis indicated the presence of the desired peak. There are no solids formed after dilution with diethyl ether. Then, the solvent was removed under vacuum. The brown solid residue was dissolved in minimum methanol and then it was diluted with diethyl ether. The resulting solution was stored in the refrigerator for 15 h, but there were no solids formed. Then, the solvent was removed under vacuum and the brown residue was purified using an ISCO (80 g) column chromatography eluting with 0-50% ethyl acetate in hexanes. The desired fractions were combined and the solvent was removed under vacuum to obtain 416 mg (43% yield) of 3-(cyclopentylamino)-2-(3-methoxynaphthalen-2-yl)-1H-imidazo[1,2-b]pyrazole-7-carbonitrile as an off-white solid. LC/MS calcd. for C22H21N5O (m/e) 371.44, obsd. 372.0 (M+H, ES+).

Workup

  1. customThen, the solvent was removed under vacuum
  2. dissolutionThe brown solid residue was dissolved in minimum methanol
  3. additionit was diluted with diethyl ether
  4. waitThe resulting solution was stored in the refrigerator for 15 h
  5. customformed
  6. customThen, the solvent was removed under vacuum
  7. customthe brown residue was purified
  8. washeluting with 0-50% ethyl acetate in hexanes
  9. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-96e2b240045442f89906a24ce09df383
Source dataset
uspto-grants-2015_10
Patent number
US09169215B2

Reaction notes

Loading…