1H-Benzotriazol-1-ol--ammonia (1/1) → HCID 117840516, compound

HRID 714825Notes

Reaction equation

HRID 714825 reaction equation
[CH3:1][C:2]([N:7]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[N:8]1)([CH3:6])[C:3](O)=[O:4].Cl.C([N:18]=C=NCCCN(C)C)C.N.ON1C2C=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:1][C:2]([N:7]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[N:8]1)([CH3:6])[C:3]([NH2:18])=[O:4]

Participants

6

Reactant 4

HCID 1131751H-Benzotriazol-1-ol--ammonia (1/1)HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7017087α,α-Dimethyl-4-nitro-1H-pyrazole-1-acetic acid

Product 1

HCID 117840516HCID 117840516, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-methyl-2-(4-nitro-1H-pyrazol-1-yl)propanoic acid (1.2 g) obtained in Step A of Example 109 in N,N-dimethylformamide (10 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.3 g) and 1-hydroxybenzotriazole ammonia salt (1.4 g), and the mixture was stirred overnight at room temperature. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate) to give the title compound (1.0 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate)

Sources & evidence

ORD record
ord-9282b33823e94f81870ff8ea6015fa57
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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