Sodium Azide → HCID 86628630, compound

HRID 1929750Notes

Reaction equation

HRID 1929750 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[N:10][C:11]2[N:12]([N:21]=[C:22](S(C)(=O)=O)[C:23]=2[C:24](=[O:31])[NH:25][CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1.[N-:36]=[N+:37]=[N-:38].[Na+]>CN(C)C=O.[Cl-].[Na+].O>[N:36]([C:22]1[C:23]([C:24](=[O:31])[NH:25][CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)=[C:11]2[N:10]=[CH:9][C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])=[C:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[N:12]2[N:21]=1)=[N+:37]=[N-:38]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 67272830HCID 67272830, compound

Product 1

HCID 86628630HCID 86628630, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of the compound obtained in Example 33 (1.5 g) in dimethylformamide (20 mL) was added sodium azide (1.11 g) and the mixture was stirred at 110° C. overnight. After cooling to room temperature, to the reaction mixture was a saturated brine and the mixture was stirred and extracted with ethyl acetate. The organic layer was washed with water and concentrated in vacuo and the resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=80/20 to 30/70) to give 2-azido-6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-(N-cyclopentylcarbamoyl)pyrazolo[1,5-a]pyrimidine (1.15 g, a yellow viscidity). To a solution of the product (870 mg) in tetrahydrofuran (16 mL) was added triphenylphosphine (896 mg) and the mixture was stirred at 40° C. for 1 hour. After cooling to room temperature, the reaction mixture was concentrated in vacuo and the resultant crude product was purified by a column chromatography on silica gel (solvent; chloroform/methanol=100/0 to 97/3) to give 6-(2-chlorophenyl)-7-(4-chlorophenyl)-2-triphenylphosphoranylidenamino-pyrazolo[1,5-a]pyrimidine (942 mg, yield: 58%) as a yellow solid MS (APCI)m/z; 726/728 M+H]+

Workup

  1. temperatureAfter cooling to room temperature, to the reaction mixture
  2. stirringthe mixture was stirred
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. concentrationconcentrated in vacuo
  6. customthe resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=80/20 to 30/70)

Sources & evidence

ORD record
ord-6e446e120531463193c75084435f70bb
Source dataset
uspto-grants-2012_05
Patent number
US08188097B2

Reaction notes

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