4-Methylmorpholine → HCID 178458414, compound

HRID 2236791Notes

Reaction equation

HRID 2236791 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]\[NH:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:26][CH2:27][CH2:28][CH3:29])=[C:21]([CH:25]=1)[C:22](O)=[O:23].O.O[N:32]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.CN1CCOCC1>CN(C)C=O.[OH-].[NH4+].O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]\[NH:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:26][CH2:27][CH2:28][CH3:29])=[C:21]([CH:25]=1)[C:22]([NH2:32])=[O:23]

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 178458415HCID 178458415, compound

Product 1

HCID 178458414HCID 178458414, compoundYield 57.1%

Reagents, catalysts & solvents 3

HCID 14923Ammonium HydroxideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-({[(Z)-(6-bromo-1,3-dioxo-2,3-dihydroisoquinolin-4(1H)-ylidene)methyl]amino}methyl)-2-propoxybenzoic acid (30 mg, 65 μmol) in N,N-dimethylformamide (1 mL) is added 1-hydroxybenzotriazole hydrate (22 mg, 0.16 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (31 mg, 0.16 mmol), and 1-methylmorpholine (25 μL, 0.23 mmol). After shaking at room temperature for 1 hour, to the reaction mixture is added 30% aqueous ammonium hydroxide (5 drops). After 10 minutes of agitation, water is added to the mixture, precipitating a solid, which is collected by filtration, washed with water and methanol, and then dried under house vacuum to give 5-({[(Z)-(6-bromo-1,3-dioxo-2,3-dihydroisoquinolin-4(1H)-ylidene)methyl]amino}methyl)-2-propoxybenzamide (17 mg, 57%).

Workup

  1. customprecipitating a solid, which
  2. filtrationis collected by filtration
  3. washwashed with water and methanol
  4. customdried under house vacuum

Sources & evidence

ORD record
ord-39bd77ae7aed4670a54799a76b046d17
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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