Perchloric Acid → HCID 178486413, compound

HRID 1754078Notes

Reaction equation

HRID 1754078 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[C:7]#[N:8].[CH3:9][O:10][C:11]1[CH:19]=[C:18]2[C:14]([CH2:15][CH2:16][CH2:17]2)=[CH:13][C:12]=1[CH:20]=O.[CH:22]1([N+:27]#[C-:28])[CH2:26][CH2:25][CH2:24][CH2:23]1.Cl(O)(=O)(=O)=O>CO>[CH:22]1([NH:27][C:28]2[N:6]3[N:5]=[CH:4][C:3]([C:7]#[N:8])=[C:2]3[NH:1][C:20]=2[C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][C:11]=2[O:10][CH3:9])[CH2:17][CH2:16][CH2:15]3)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 24247Perchloric AcidHCID 855155-Amino-4-cyanopyrazoleHCID 2734784Cyclopentyl IsocyanideHCID 31596856-Methoxy-indan-5-carbaldehyde

Product 1

HCID 178486413HCID 178486413, compoundYield 8.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 5-amino-1H-pyrazole-4-carbonitrile (193 mg, 1.79 mmol) and 6-methoxy-2,3-dihydro-1H-indene-5-carbaldehyde (315 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 light yellow suspension was stirred for 15 h and the resulting solids were collected by filtration and washed with methanol. After air drying, 55 mg (8.5% yield) of 3-(cyclopentylamino)-2-(6-methoxy-2,3-dihydro-1H-inden-5-yl)-1H-imidazo[1,2-b]pyrazole-7-carbonitrile was isolated as an off-white solid. LC/MS calcd. for C21H23N5O (m/e) 361.44, obsd. 362.1 (M+H, ES+).

Workup

  1. filtrationthe resulting solids were collected by filtration
  2. washwashed with methanol
  3. customAfter air drying

Sources & evidence

ORD record
ord-a8c55e91fc2143f59c4e608062d8fe4e
Source dataset
uspto-grants-2015_10
Patent number
US09169215B2

Reaction notes

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