HCID 24993829, compound → 8-iodo-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

HRID 1914737Notes

Reaction equation

HRID 1914737 reaction equation
[I:1][C:2]1[N:11]=[CH:10][C:9]2[CH2:8][CH2:7][C:6]3[C:12]([C:16]([O-:18])=O)=[N:13][N:14]([CH3:15])[C:5]=3[C:4]=2[N:3]=1.[K+].[N:20]1(C([O-])=O)C2C=CC=CC=2N=N1.[NH4+]>CN(C)C=O.O>[I:1][C:2]1[N:11]=[CH:10][C:9]2[CH2:8][CH2:7][C:6]3[C:12]([C:16]([NH2:20])=[O:18])=[N:13][N:14]([CH3:15])[C:5]=3[C:4]=2[N:3]=1

Participants

5

Reactant 2

HCID 24993829HCID 24993829, compoundHCID 57454228ammonium 1H-1,2,3-benzotriazol-1-ate

Product 1

HCID 442356528-iodo-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamideYield 90.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of potassium 8-iodo-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate (394 mg, 1.0 mmol) in anhydrous dimethylformamide (10 mL) was treated with N-ethyl-N′,N′-diisopropyl carbodiimide hydrochloride (EDCI) (287 mg, 1.5 mmol) and with ammonium 1H-1,2,3-benzotriazol-1-ate (304 mg, 2 mmol). The reaction was stirred at room temperature overnight. The reaction was diluted with water and the resulting precipitate was collected by filtration to afford the title compound (320 mg, 90% yield).

Workup

  1. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-51cd962675ac4a50b608350d46b10ea2
Source dataset
uspto-grants-2013_12
Patent number
US08614220B2

Reaction notes

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