1-Hydroxybenzotriazole → HCID 86683891, compound

HRID 2406768Notes

Reaction equation

HRID 2406768 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[NH:13][C:14](=[O:22])[C:15]([F:21])=[CH:16][C:17]=2[C:18]([OH:20])=O)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.CC[N:25]=C=NCCCN(C)C.Cl.[CH:35]1[CH:36]=[CH:37][C:38]2[N:43](O)[N:42]=[N:41][C:39]=2[CH:40]=1.O.N>C(OCC)(=O)C.CN(C=O)C.O>[N:41]1([O:22][C:14]2[C:15]([F:21])=[CH:16][C:17]([C:18]([NH2:25])=[O:20])=[C:12]([NH:11][C:5]3[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[N:13]=2)[C:39]2[CH:40]=[CH:35][CH:36]=[CH:37][C:38]=2[N:43]=[N:42]1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12896473Azane;hydrateHCID 86683892HCID 86683892, compound

Product 1

HCID 86683891HCID 86683891, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(3,5-dimethoxyphenylamino)-5-fluoro-6-oxo-1,6-dihydropyridin-3-carboxylic acid (200 mg), WSC.HCl (312 mg), HOBt.H2O (249 mg), and DMF (2 ml) was stirred at room temperature for 45 minutes. 25% ammonia water (1 ml) was added, followed by stirring at the same temperature for 2 hours. Ethyl acetate was added to the reaction mixture. The resultant was washed with saturated saline and dried over anhydrous magnesium sulfate, the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=7:3 to 1:1), and a yellow solid of 6-(1H-1,2,3-benzotriazol-1-yloxy)-2-(3,5-dimethoxyphenylamino)-5-fluoronicotinamide (109 mg) was thus obtained.

Workup

  1. washThe resultant was washed with saturated saline
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled away under reduced pressure
  4. customThe obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=7:3 to 1:1)

Sources & evidence

ORD record
ord-910975186f6540c49864b3a97dd934c3
Source dataset
uspto-grants-2014_08
Patent number
US08809371B2

Reaction notes

Loading…