Sodium Iodide → HCID 73854977, compound

HRID 2121986Notes

Reaction equation

HRID 2121986 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[C:14]2[N:18]([CH3:19])[C:17]3[CH:20]=[C:21]([O:24][CH2:25][CH2:26]Cl)[CH:22]=[CH:23][C:16]=3[S:15]2)[S:10][C:9]1=[N:28][C:29]1[CH:30]=[C:31]([NH:38][C:39](=[O:44])[CH2:40][N:41]([CH3:43])[CH3:42])[CH:32]=[CH:33][C:34]=1[NH:35][CH2:36][CH3:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.[N-:50]=[N+:51]=[N-:52].[Na+].[I-].[Na+]>CCOC(C)=O>[N:50]([CH2:26][CH2:25][O:24][C:21]1[CH:22]=[CH:23][C:16]2[S:15][C:14](=[C:11]3[S:10][C:9](=[N:28][C:29]4[CH:30]=[C:31]([NH:38][C:39](=[O:44])[CH2:40][N:41]([CH3:43])[CH3:42])[CH:32]=[CH:33][C:34]=4[NH:35][CH2:36][CH3:37])[N:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:12]3=[O:13])[N:18]([CH3:19])[C:17]=2[CH:20]=1)=[N+:51]=[N-:52]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 33557Sodium AzideHCID 73854978HCID 73854978, compound

Product 1

HCID 73854977HCID 73854977, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a 50 mL flask was added the product of Example 145 (225 mg, 345 μmol), anhydrous DMF (8 mL), sodium azide (112 mg, 1.73 mmol), and sodium iodide (15 mg, 103 μmol). The reaction slurry was heated at 70° C. for 6 h under N2. The reaction mixture was diluted with EtOAc (70 mL), washed with H2O (2×30 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to provide the title compound. MS(ESI): 658 (MH+).

Workup

  1. washwashed with H2O (2×30 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ae7143b0b8004d3c90b0f7fabbfe4113
Source dataset
uspto-grants-2004_02
Patent number
US06696473B2

Reaction notes

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