2,4,5-Trimethoxybenzaldehyde → HCID 178493432, compound

HRID 1754074Notes

Reaction equation

HRID 1754074 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[CH:7][C:4]=1[CH:5]=O.[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>[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:5]=2[C:4]2[CH:7]=[C:8]([O:13][CH3:14])[C:9]([O:11][CH3:12])=[CH:10][C:3]=2[O:2][CH3:1])[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 205252,4,5-TrimethoxybenzaldehydeHCID 24247Perchloric AcidHCID 855155-Amino-4-cyanopyrazoleHCID 2734784Cyclopentyl Isocyanide

Product 1

HCID 178493432HCID 178493432, compoundYield 14.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a clear light brown solution of 2,4,5-trimethoxybenzaldehyde (600 mg, 3.06 mmol) and 5-amino-1H-pyrazole-4-carbonitrile (331 mg, 3.06 mmol) in methanol (10 mL) in a 20 mL vial were added cyclopentyl isonitrile (294 mg, 342 μL, 3.06 mmol) and perchloric acid (61.4 mg, 54.9 μL, 0.612 mmol) at RT under nitrogen atmosphere. Then, the nitrogen line was disconnected and the resulting dark brown solution slowly became a suspension within few hours which was then stirred for 15 h at RT. The off-white solids were collected by filtration and washed with methanol and the solids were not the desired product. The filtrate was removed under vacuum and the resulting residue was purified using an ISCO (120 g) column chromatography eluting with 0-60% ethyl acetate in hexanes. The desired fractions were combined and the solvent was removed under vacuum to isolate 165 mg (14% yield) of 3-(cyclopentylamino)-2-(2,4,5-trimethoxyphenyl)-1H-imidazo[1,2-b]pyrazole-7-carbonitrile as a dark brown solid. LC/MS calcd. for C20H23N5O3 (m/e) 381.434, obsd. 382.1 (M+H, ES+).

Workup

  1. filtrationThe off-white solids were collected by filtration
  2. washwashed with methanol
  3. customThe filtrate was removed under vacuum
  4. customthe resulting residue was purified
  5. washeluting with 0-60% ethyl acetate in hexanes
  6. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-db528a43d9954550b8b02f023d031f29
Source dataset
uspto-grants-2015_10
Patent number
US09169215B2

Reaction notes

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