Water → HCID 178488546, compound

HRID 873522Notes

Reaction equation

HRID 873522 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([C:15]#[N:16])[CH:12]=[CH:11][CH:10]=2)=[CH:5][C:4]=1[CH:17]1[C:30]2[C:29](=[O:31])[CH2:28][C:27]([CH3:33])([CH3:32])[CH2:26][C:25]=2[O:24][C:23]2[CH2:22][C:21]([CH3:35])([CH3:34])[CH2:20][C:19](=[O:36])[C:18]1=2.[N-:37]=[N+:38]=[N-:39].[Na+].[Cl-].[NH4+].O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([C:15]3[NH:39][N:38]=[N:37][N:16]=3)[N:14]=2)=[CH:5][C:4]=1[CH:17]1[C:30]2[C:29](=[O:31])[CH2:28][C:27]([CH3:32])([CH3:33])[CH2:26][C:25]=2[O:24][C:23]2[CH2:22][C:21]([CH3:35])([CH3:34])[CH2:20][C:19](=[O:36])[C:18]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 117700637HCID 117700637, compound

Product 1

HCID 178488546HCID 178488546, compoundYield 9.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of the 6-[4-methoxy-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyridine-2-carbonitrile produced in Example 6 (500 mg, 1.04 mmol), sodium azide (76.4 mg, 1.14 mmol), and ammonium chloride (61.0 mg, 1.14 mmol) in DMF (10 ml) was prepared at room temperature, and the suspension thus prepared was then stirred at 80° C. for 4 hours. After air-cooling, water was added to the reaction solution, and the mixed solution was then extracted with ethyl acetate. The organic layer thus obtained was dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, and the residue thus obtained was then purified by silica gel column chromatography (ethyl acetate:hexane=66:34, v/v, methanol:dichloromethane=3:97 to 5:95, v/v). The solid thus obtained was washed with a mixed solution of diethyl ether and hexane, followed by collection by filtration and drying, to obtain the title compound (51 mg, yield: 9.4%).

Workup

  1. customwas prepared at room temperature
  2. customthe suspension thus prepared
  3. temperatureAfter air-cooling
  4. extractionthe mixed solution was then extracted with ethyl acetate
  5. customThe organic layer thus obtained
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled away under reduced pressure
  8. customthe residue thus obtained
  9. customwas then purified by silica gel column chromatography (ethyl acetate:hexane=66:34, v/v, methanol:dichloromethane=3:97 to 5:95, v/v)
  10. customThe solid thus obtained
  11. washwas washed with a mixed solution of diethyl ether and hexane
  12. filtrationfollowed by collection by filtration
  13. customdrying

Sources & evidence

ORD record
ord-33785014bc5e4485b965794b41c7dfcd
Source dataset
uspto-grants-2015_03
Patent number
US08975263B2

Reaction notes

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