Water → 4-(6-fluoro-3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)-N-(pyrrolidin-1-yl-butyl)benzamide

HRID 1817058Notes

Reaction equation

HRID 1817058 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][CH2:35][CH2:36][CH2:37][CH2:38][N:39]1[CH2:43][CH2:42][CH2:41][CH2:40]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][CH2:35][CH2:36][CH2:37][CH2:38][N:39]5[CH2:43][CH2:42][CH2:41][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 27627624-(Pyrrolidin-1-yl)butan-1-amineHCID 589748584-(6-fluoro-3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)benzoyl chloride

Product 1

HCID 589748984-(6-fluoro-3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)-N-(pyrrolidin-1-yl-butyl)benzamideYield 38.2%

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 1-(4-aminobutyl)pyrrolidine (41 mg). The mixture was stirred at room temperature 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). The volatiles were removed under vacuum. The product was isolated as a brown powder (50 mg, 0.11 mmol, 37%). LCMS: m/z [M+H]+ 463.

Workup

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

Sources & evidence

ORD record
ord-24a645dd881c4c5992f2b5d08adb9f0b
Source dataset
uspto-grants-2009_10
Patent number
US07598247B2

Reaction notes

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