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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 2192495
Notes
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Reaction equation

HRID 2192495 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 225977283-Chloro-4-(propan-2-yloxy)benzoic acidHCID 178418300HCID 178418300, compoundHCID 178513275HCID 178513275, compound

Product 1

HCID 581499065-[5-[3-Chloro-4-(1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl]-1(2H)-isoquinolinone
Yield 50.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. stirringthe suspension was stirred at room temperature for 2 hours
  2. stirringstirred for 1 hour
  3. customThe solvent was evaporated
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes