1-Hydroxybenzotriazole → HCID 117652373, compound

HRID 1428407Notes

Reaction equation

HRID 1428407 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([N:14]([CH3:19])[CH2:15][C:16](O)=O)=[O:13])[C:6]=2[CH:20]=1.[Cl:21][C:22]1[CH:23]=[C:24]([NH2:30])[C:25]([NH2:29])=[CH:26][C:27]=1[Cl:28].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CCOC(C)=O.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([N:14]([CH2:15][C:16]3[NH:29][C:25]4[CH:26]=[C:27]([Cl:28])[C:22]([Cl:21])=[CH:23][C:24]=4[N:30]=3)[CH3:19])=[O:13])[C:6]=2[CH:20]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 792974,5-Dichloro-1,2-phenylenediamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 117652690HCID 117652690, compound

Product 1

HCID 117652373HCID 117652373, compoundYield 41.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of N-[(5-chloro-2-oxo-1,3-benzothiazol-3(2H)-yl)acetyl]-N-methylglycine (90 mg), 4,5-dichlorobenzene-1,2-diamine (53 mg), and DMF (3 mL) were added TEA (95 μL), HOBt (43 mg), and WSC.HCl (60 mg), followed by stirring at room temperature overnight. The reaction mixture was diluted with EtOAc. The organic layer was washed with water, a saturated aqueous NaHCO3 solution, and brine in this order, dried over Na2SO4, and then concentrated under reduced pressure. To the residue was added acetic acid (3 mL), followed by heating and stirring at 110° C. for 5 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The residue was diluted with EtOAc. The organic layer was washed with a saturated aqueous NaHCO3 solution and brine in this order, dried over Na2SO4, and then concentrated under reduced pressure. The resulting solid was collected by filtration and then washed with MeOH to obtain 2-(5-chloro-2-oxo-1,3-benzothiazol-3(2H)-yl)-N-[(5,6-dichloro-1H-benzimidazol-2-yl)methyl]-N-methylacetamide (54 mg).

Workup

  1. washThe organic layer was washed with water
  2. dry with materiala saturated aqueous NaHCO3 solution, and brine in this order, dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue was added acetic acid (3 mL)
  5. temperatureby heating
  6. stirringstirring at 110° C. for 5 hours
  7. temperatureThe reaction mixture was cooled to room temperature
  8. concentrationconcentrated under reduced pressure
  9. additionThe residue was diluted with EtOAc
  10. washThe organic layer was washed with a saturated aqueous NaHCO3 solution and brine in this order
  11. dry with materialdried over Na2SO4
  12. concentrationconcentrated under reduced pressure
  13. filtrationThe resulting solid was collected by filtration
  14. washwashed with MeOH

Sources & evidence

ORD record
ord-81dafec6a3034d7daf227170f43a68fc
Source dataset
uspto-grants-2015_01
Patent number
US08937087B2

Reaction notes

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