Water → HCID 23442367, compound

HRID 2119662Notes

Reaction equation

HRID 2119662 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]1[C:13]2[CH:12]=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=2[C:7](=[O:15])[C:6]2[N:16]([CH3:19])[N:17]=[CH:18][C:5]1=2.[N-:20]=[N+]=[N-].[Na+].O>CN(C)C=O>[ClH:1].[NH2:20][CH2:2][CH2:3][N:4]1[C:13]2[CH:12]=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=2[C:7](=[O:15])[C:6]2[N:16]([CH3:19])[N:17]=[CH:18][C:5]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 23442445HCID 23442445, compound

Product 1

HCID 23442367HCID 23442367, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-(2-chloroethyl)-1,7-dimethyl-1,4-dihydro-9H-pyrazolo[4,3-b]quinolin-9-one (EXAMPLE 62, step 3, 109 mg, 0.396 mmol) in N,N-dimethylformamide (7 ml) was added sodium azide (77 mg, 1.2 mmol) at room temperature. The resulting mixture was heated at 70° C. for 9.5 h. After cooling to room temperature, water (50 ml) was added and extracted with ethyl acetate (50 ml×3). The combined organic layer was dried over magnesium sulfate and concentrated in vacuo to give 110 mg (99%) of the title compound as a yellow solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate (50 ml×3)
  3. dry with materialThe combined organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9bafd0c60502407f99fbdcad496f968f
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Reaction notes

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