Ammonia → HCID 68712548, compound

HRID 1913198Notes

Reaction equation

HRID 1913198 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[N:12]=[CH:11][C:10]([C:13]([Cl:15])=[O:14])=[CH:9][CH:8]=2)[NH:5][CH:4]=[C:3]1[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1.[NH3:22]>O1CCOCC1>[ClH:15].[O:1]=[C:2]1[N:6]([C:7]2[N:12]=[CH:11][C:10]([C:13]([NH2:22])=[O:14])=[CH:9][CH:8]=2)[NH:5][CH:4]=[C:3]1[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 59280170HCID 59280170, compound

Product 1

HCID 68712548HCID 68712548, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

337 mg (1.0 mmol) of 6-(5-oxo-4-pyridin-3-yl-2,5-dihydro-1H-pyrazol-1-yl)pyridine-3-carbonyl chloride are suspended in 5 ml of dioxane. Slowly and with stirring, 4 ml of a 5 N solution of ammonia in dioxane are then added, and the mixture is stirred at RT for 16 h. The mixture is then concentrated, and the residue is taken up in DMSO and purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with 0.1% TFA added to the water). The product-containing fractions are combined and concentrated on a rotary evaporator. The residue is dissolved in 1 N hydrochloric acid, and the solution is then lyophilized.

Workup

  1. stirringthe mixture is stirred at RT for 16 h
  2. concentrationThe mixture is then concentrated
  3. custompurified by preparative HPLC (RP18 column
  4. additionmobile phase: acetonitrile/water gradient with 0.1% TFA added to the water)
  5. concentrationconcentrated on a rotary evaporator
  6. dissolutionThe residue is dissolved in 1 N hydrochloric acid

Sources & evidence

ORD record
ord-74953f110d6f4725b29bfe7c62b93e0a
Source dataset
uspto-grants-2013_12
Patent number
US08609698B2

Reaction notes

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