1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 5-[5-[3-Chloro-4-(1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl]-1(2H)-isoquinolinone

HRID 2192495Notes

Reaction equation

Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.[Cl:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[O:33][CH:34]([CH3:36])[CH3:35])[C:27]([OH:29])=O.O[NH:38][C:39]([C:41]1[C:42]2[CH:43]=[CH:44][NH:45][C:46](=[O:51])[C:47]=2[CH:48]=[CH:49][CH:50]=1)=[NH:40]>CN(C=O)C>[Cl:23][C:24]1[CH:25]=[C:26]([C:27]2[O:29][N:40]=[C:39]([C:41]3[CH:50]=[CH:49][CH:48]=[C:47]4[C:42]=3[CH:43]=[CH:44][NH:45][C:46]4=[O:51])[N:38]=2)[CH:30]=[CH:31][C:32]=1[O:33][CH:34]([CH3:36])[CH3:35]

Participants

Conditions

Temperature: 140 °C

Procedure

1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI; 5.2 g) and hydroxybenzotriazole (HOBt; 3.6 g) were added to a solution of 3-chloro-4-[(1-methylethyl)oxy]benzoic acid (D3; 2.9 g) in DMF (200 ml) at room temperature, and the resulting solution was stirred for 30 minutes. N-hydroxy-1-oxo-1,2-dihydro-5-isoquinolinecarboximidamide (D37, 2.75 g) was added and the suspension was stirred at room temperature for 2 hours. The reaction mixture was heated to 140° C. and stirred for 1 hour. The solvent was evaporated and the residue was washed with water, followed by ethyl acetate to give the title compound (2.6 g).

Workup

stirringthe suspension was stirred at room temperature for 2 hours
stirringstirred for 1 hour
customThe solvent was evaporated
washthe residue was washed with water

Sources & evidence

ORD record: ord-43d1fbcebbb647c5901c5e74010cda9c
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329730B2

Reaction notes

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