Water → HCID 58974915, compound

HRID 1817059Notes

Reaction equation

HRID 1817059 reaction equation
[F:1][C:2]1[C:11]2[N:10]=[N:9][C:8]3[C:12](=[O:24])[N:13]([C:15]4[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=4)[NH:14][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[NH2:34][CH:35]1[CH2:40][C:39]([CH3:42])([CH3:41])[N:38]([CH3:43])[C:37]([CH3:45])([CH3:44])[CH2:36]1.O>CC(N(C)C)=O.C(O)CCC>[F:1][C:2]1[C:11]2[N:10]=[N:9][C:8]3[C:12](=[O:24])[N:13]([C:15]4[CH:23]=[CH:22][C:18]([C:19]([NH:34][CH:35]5[CH2:36][C:37]([CH3:44])([CH3:45])[N:38]([CH3:43])[C:39]([CH3:42])([CH3:41])[CH2:40]5)=[O:20])=[CH:17][CH:16]=4)[NH:14][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 6937924-Amino-1,2,2,6,6-pentamethylpiperidineHCID 589748584-(6-fluoro-3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)benzoyl chloride

Product 1

HCID 58974915HCID 58974915, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 31374DimethylacetamideSolvent

Procedure

4-(6-fluoro-3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)benzoyl chloride (100 mg, 0.29 mmol) was dissolved in anhydrous DMA (2 ml). Diisopropylethylamine (75 mg, 101 μl, 0.58 mmol) was added followed by 4-amino-1,2,2,6,6-pentamethylpiperidine (49 mg, 0.29 mmol). The mixture was stirred overnight. Water (5 ml) and n-butanol (5 ml) were added. The phases were separated. The organic phase was washed with water (2×5 ml) and the solution was concentrated under vacuum. The title compound was isolated as a dark red solid (50 mg, 0.105 mmol, 36%). LCMS: m/z [M+H]+ 477.

Workup

  1. customThe phases were separated
  2. washThe organic phase was washed with water (2×5 ml)
  3. concentrationthe solution was concentrated under vacuum

Sources & evidence

ORD record
ord-a8cfd42e36414202922b982e7ecf519f
Source dataset
uspto-grants-2009_10
Patent number
US07598247B2

Reaction notes

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