Ammonium Chloride → HCID 178505750, compound

HRID 1289979Notes

Reaction equation

HRID 1289979 reaction equation
[CH2:1]([O:8][C@@H:9]1[CH2:13][CH2:12][C@@H:11]([CH2:14][C:15]#[N:16])[C@H:10]1[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:24]=[N+:25]=[N-:26].[Na+].[Cl-].[NH4+]>CN(C=O)C.O>[CH2:1]([O:8][C@@H:9]1[CH2:13][CH2:12][C@@H:11]([CH2:14][C:15]2[NH:26][N:25]=[N:24][N:16]=2)[C@H:10]1[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 22885656HCID 22885656, compound

Product 1

HCID 178505750HCID 178505750, compoundYield 64.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

To a solution of 342 mg of product from Step D in 7 mL of DMF was added 215 mg of sodium azide and 176 mg of ammonium chloride. The reaction was heated at 125° C. for 4 days and then cooled and diluted with water and extracted twice with ether. The organic layers were washed with a portion of brine, combined, dried over sodium sulfate and evaporated. The residue was purified by flash chromatography with 5% methanol in methylene chloride to obtain 250 mg of title compound as a oil. T.l.c. (5% methanol in methylene chloride) Rf =0.2. Mass spec (NH3 /CI): 353(M+1).

Workup

  1. temperaturecooled
  2. extractionextracted twice with ether
  3. washThe organic layers were washed with a portion of brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue was purified by flash chromatography with 5% methanol in methylene chloride

Sources & evidence

ORD record
ord-37cea8ee1ec44373a3434d16cfe14c36
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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