Dimethylamine → HCID 68190287, compound

HRID 513779Notes

Reaction equation

HRID 513779 reaction equation
[CH3:1][NH:2][CH3:3].[Cl:4][C:5]1[CH:6]=[C:7]2[C:16](=[C:17]3[C:22]=1[CH:21]=[CH:20][CH:19]=[N:18]3)[NH:15][S:14](=[O:24])(=[O:23])[C:13]1[C:8]2=[CH:9][C:10]([C:25](O)=[O:26])=[CH:11][CH:12]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O.C(Cl)Cl>[CH3:1][N:2]([CH3:3])[C:25]([C:10]1[CH:9]=[C:8]2[C:13]([S:14](=[O:24])(=[O:23])[NH:15][C:16]3[C:7]2=[CH:6][C:5]([Cl:4])=[C:22]2[C:17]=3[N:18]=[CH:19][CH:20]=[CH:21]2)=[CH:12][CH:11]=1)=[O:26]

Participants

8

Reactant 4

HCID 674DimethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68190302HCID 68190302, compound

Product 1

HCID 68190287HCID 68190287, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Dimethyl amine (0.2M in THF, 2.77 ml, 0.69 mmol) was added to a solution of 12-chloro-6,6-dioxo-5,6-dihydro-6λ*6*-thia-4,5-diaza-chrysene-9-carboxylic acid 524 (100 mg, 0.27 mmol), EDC.HCl (80 mg, 0.41 mmol), HOBt (56 mg, 0.41 mmol) and TEA (0.12 ml, 0.83 mmol) in DMF (1 ml) and the mixture was stirred at room temperature for 12 h. The mixture was diluted with water and DCM. The organic phase was dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with chloroform/MeOH (95:5) as the eluent to give the title compound (45 mg, 42%).

Workup

  1. dry with materialThe organic phase was dried (Na2SO4)
  2. concentrationconcentrated in vacuo
  3. customThe crude residue was purified by column chromatography with chloroform/MeOH (95:5) as the eluent

Sources & evidence

ORD record
ord-88784772e8c94a8ca53af408fee8a95c
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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