Hexane → HCID 131730950, compound

HRID 2035494Notes

Reaction equation

HRID 2035494 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:32]=[C:33]([F:35])[CH:34]=1)[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22]OS(C)(=O)=O)=[CH:16][CH:15]=2)[N:10]=[CH:9][C:8]=1[CH2:28][C:29]([NH2:31])=[O:30].[N-:36]=[N+:37]=[N-:38].[Na+].CCCCCC>CN(C)C=O>[N:36]([CH2:22][CH2:21][CH2:20][C:17]1[CH:16]=[CH:15][C:14]([NH:13][C:11]2[N:10]=[CH:9][C:8]([CH2:28][C:29]([NH2:31])=[O:30])=[C:7]([NH:6][CH2:5][C:4]3[CH:32]=[C:33]([F:35])[CH:34]=[C:2]([F:1])[CH:3]=3)[CH:12]=2)=[CH:19][CH:18]=1)=[N+:37]=[N-:38]

Participants

5

Reactant 3

HCID 8058HexaneHCID 33557Sodium AzideHCID 131730951HCID 131730951, compound2×

Product 1

HCID 131730950HCID 131730950, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

268 mg of 4-[(3,5-difluorobenzyl)amino]-6-{[4-(3-methanesulfonyloxypropyl)phenyl]amino}pyridine-3-carboxyamide (the compound of Example 199) was dissolved in 1.5 mL of N,N-dimethylformamide, to which 71 mg of sodium azide was added and stirred at 80° C. for 30 minutes. After cooling, hexane was added to the reaction mixture, and the deposit was filtered. The filtered product was dissolved in chloroform, washed with water and saturated saline, and dried on anhydrous sodium sulfate. By evaporating the solvent, 229 mg (94%) of the title compound was obtained as a slight yellow crystalline powder.

Workup

  1. additionwas added
  2. temperatureAfter cooling
  3. filtrationthe deposit was filtered
  4. dissolutionThe filtered product was dissolved in chloroform
  5. washwashed with water and saturated saline
  6. dry with materialdried on anhydrous sodium sulfate
  7. customBy evaporating the solvent

Sources & evidence

ORD record
ord-d451889c1ce841349cade1680966d695
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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