3-Chloroaniline → N-(3-chlorophenyl)-4-oxo-1-propyl-4,5-dihydro[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxamide

HRID 1807871Notes

Reaction equation

[O:1]=[C:2]1[NH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([OH:14])=O)[CH:9]=2)[N:4]2[C:15]([CH2:18][CH2:19][CH3:20])=[N:16][N:17]=[C:3]12.[Cl:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=1)[NH2:25].ON1C2C=CC=CC=2N=N1.N=C=N.C(=O)([O-])[O-].[N-]=C=O>CN(C)C=O.C(N(CC)CC)C>[Cl:21][C:22]1[CH:23]=[C:24]([NH:25][C:12]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[N:4]2[C:15]([CH2:18][CH2:19][CH3:20])=[N:16][N:17]=[C:3]2[C:2](=[O:1])[NH:11]3)=[O:14])[CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 8.2 mg of 4-oxo-1-propyl-4,5-dihydro[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxylic acid, 1.6 mg of 3-chloroaniline, 4.1 mg of 1-hydroxybenzotriazole, 8.4 μL of triethylamine, and 1 mL of N,N-dimethylformamide was added 100 mg of PS-Carbodiimide (Biotage AB), followed by stirring at 60° C. overnight. To the reaction mixture were added 50 mg of MP-Carbonate (Biotage AB) and 50 mg of PS-Isocyanate (Biotage AB) at room temperature, followed by stirring for 4 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The obtained residue was purified by preparative HPLC (methanol/0.1% aqueous formic acid solution) to obtain 0.87 mg of N-(3-chlorophenyl)-4-oxo-1-propyl-4,5-dihydro[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxamide.

Workup

stirringby stirring for 4 hours
filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated under reduced pressure
customThe obtained residue was purified by preparative HPLC (methanol/0.1% aqueous formic acid solution)

Sources & evidence

ORD record: ord-99d8606378204799bd6d3367b638457c
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357688B2

Reaction notes

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