Sodium Iodide → HCID 73854977, compound

HRID 1242017Notes

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

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

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

Sources & evidence

ORD record: ord-2f1acf6f535a44f48e5f421bf483ace5
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115640B2

Reaction notes

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