3,4,5-Trimethoxybenzaldehyde → HCID 178488044, compound

HRID 1754082Notes

Reaction equation

HRID 1754082 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH:6]=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:6]=2[C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=2)[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 24247Perchloric AcidHCID 855155-Amino-4-cyanopyrazoleHCID 2734784Cyclopentyl Isocyanide

Product 1

HCID 178488044HCID 178488044, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a clear light brown solution of 3,4,5-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 brown suspension was stirred for 15 h at RT. The off-white solids were collected by filtration and washed with methanol. After drying in the air, 375 mg (32%) of 3-(cyclopentylamino)-2-(3,4,5-trimethoxyphenyl)-1H-imidazo[1,2-b]pyrazole-7-carbonitrile was isolated as an off-white solid. LC/MS calcd. for C20H23N5O3 (m/e) 381.434, obsd. 382.0 (M+H, ES+).

Workup

  1. filtrationThe off-white solids were collected by filtration
  2. washwashed with methanol
  3. customAfter drying in the air

Sources & evidence

ORD record
ord-6403a109c69f4bf2a9aa82d8a2d752bc
Source dataset
uspto-grants-2015_10
Patent number
US09169215B2

Reaction notes

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