2,6-Diethylaniline → 8-Amino-N-(2,6-diethylphenyl)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

HRID 81950

Reaction equation

HRID 81950 reaction equation
[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[CH2:8][CH2:7][C:6]3[C:12]([C:16]([OH:18])=O)=[N:13][N:14]([CH3:15])[C:5]=3[C:4]=2[N:3]=1.[K].C(N(C(C)C)C(C)C)C.ON1C2C=CC=CC=2N=N1.[CH2:39]([C:41]1[CH:47]=[CH:46][CH:45]=[C:44]([CH2:48][CH3:49])[C:42]=1[NH2:43])[CH3:40]>CN(C)C=O.O>[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[CH2:8][CH2:7][C:6]3[C:12]([C:16]([NH:43][C:42]4[C:44]([CH2:48][CH3:49])=[CH:45][CH:46]=[CH:47][C:41]=4[CH2:39][CH3:40])=[O:18])=[N:13][N:14]([CH3:15])[C:5]=3[C:4]=2[N:3]=1

Participants

7

Reactant 4

HCID 113692,6-DiethylanilineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 67076100potassium 8-amino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylic acid

Product 1

HCID 670756638-Amino-N-(2,6-diethylphenyl)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamideYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of potassium 8-amino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylic acid (180 mg, 0.73 mmol) in anhydrous dimethylformamide (5.0 mL) was treated with N-ethyl-N,N-diisopropylamine (0.258 mL, 1.47 mmol) and N-ethyl-N′,N′-diisopropyl carbodiimide hydrochloride (EDCI) (280 mg, 1.47 mmol) and 1-hydroxybenzotriazole (200 mg, 1.47 mmol). The mixture was then treated with 2,6-diethylaniline (0.170 mL, 1.1 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 (190 mg, 70% yield).

Workup

  1. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-e607a4f63824469db74a4ab864200bfa
Source dataset
uspto-grants-2014_09
Patent number
US08846701B2

Linked notes

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