Sodium Azide → HCID 10454968, compound

HRID 601164Notes

Reaction equation

HRID 601164 reaction equation
[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[C:8](Cl)=[C:7]([C:16]2[NH:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[S:18](=[O:27])(=[O:26])[N:17]=2)[C:6]1=[O:28])[CH2:2][CH2:3][CH3:4].[N-:29]=[N+:30]=[N-:31].[Na+]>CN(C)C=O>[N:29]([C:8]1[C:9]2[C:14](=[N:13][CH:12]=[CH:11][CH:10]=2)[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6](=[O:28])[C:7]=1[C:16]1[NH:21][C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[S:18](=[O:26])(=[O:27])[N:17]=1)=[N+:30]=[N-:31]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 10093388HCID 10093388, compound

Product 1

HCID 10454968HCID 10454968, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the product of Example 165 (0.1 g, 0.24 mmol) and sodium azide (0.037 g, 0.571 mmol) in dimethylformamide (2.5 ml) was stirred at 80° C. for 1.5 hours, allowed to cool to room temperature and concentrated under reduced pressure. The crude residue was purified by a C8 HPLC column eluting with 20% to 80% acetonitrile in water with 1% trifluoroacetic acid to give the title compound (0.025 g, 26% after column purification). MS (ESI−) m/z 422 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 0.94 (t, J=7.35 Hz, 3H), 1.38 (m, 2H), 1.67 (m, 2H), 4.42 (t, J=7.54 Hz, 2H), 7.41 (d, J=7.72 Hz, 1H), 7.46 (dd, J=7.91, 4.60 Hz, 1H), 7.56 (m, 1H), 7.76 (m, 1H), 7.91 (dd, J=8.09, 1.10 Hz, 1H), 8.41 (dd, J=8.09, 1.84 Hz, 1H), 8.84 (dd, J=4.41, 1.84 Hz, 1H), 12.74 (s, 1H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude residue was purified by a C8 HPLC column
  3. washeluting with 20% to 80% acetonitrile in water with 1% trifluoroacetic acid

Sources & evidence

ORD record
ord-595911a4c00543bc90995747fa6eba60
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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