Sodium Azide → HCID 178455384, compound

HRID 715597Notes

Reaction equation

HRID 715597 reaction equation
CS(O[C@H:6]1[CH2:11][CH2:10][C@@H:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:23]=[C:22]4[N:24]([CH2:44][O:45][CH2:46][CH2:47][Si:48]([CH3:51])([CH3:50])[CH3:49])[C:25]([O:27][C@@H:28]5[CH2:32][O:31][C@@H:30]6[C@H:33]([O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[CH2:34][O:35][C@H:29]56)=[N:26][C:21]4=[CH:20][C:19]=3[Cl:52])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)(=O)=O.[N-:53]=[N+:54]=[N-:55].[Na+]>CN(C)C=O>[N:53]([C@H:6]1[CH2:7][CH2:8][C@H:9]([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[N:23]=[C:22]4[N:24]([CH2:44][O:45][CH2:46][CH2:47][Si:48]([CH3:51])([CH3:49])[CH3:50])[C:25]([O:27][C@@H:28]5[CH2:32][O:31][C@@H:30]6[C@H:33]([O:36][Si:37]([C:40]([CH3:43])([CH3:41])[CH3:42])([CH3:39])[CH3:38])[CH2:34][O:35][C@H:29]56)=[N:26][C:21]4=[CH:20][C:19]=3[Cl:52])=[CH:16][CH:17]=2)[CH2:10][CH2:11]1)=[N+:54]=[N-:55]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 178455391HCID 178455391, compound

Product 1

HCID 178455384HCID 178455384, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

(cis)-4-(4-(2-((3R,3aR,6R,6aS)-6-(tert-Butyldimethylsilyloxy)hexahydrofuro[3,2-b]furan-3-yloxy)-6-chloro-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridin-5-yl)phenyl)cyclohexyl methanesulfonate (295 mg) is dissolved in N,N-dimethylformamide (5 mL), treated with sodium azide (52 mg) and stirred for 12 hours at 80° C. The mixture is partitioned between ethylacetate and saturated aqueous NH4Cl solution. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10→60:40) to give the title compound. LC (method 5): tR=1.33 min; Mass spectrum (ESI+): m/z=741 [M+H]+.

Workup

  1. customThe mixture is partitioned between ethylacetate and saturated aqueous NH4Cl solution
  2. dry with materialThe organic phase is dried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10→60:40)

Sources & evidence

ORD record
ord-9c0265382d6645a6b69eb3dfe9af8c95
Source dataset
uspto-grants-2015_11
Patent number
US09187477B2

Reaction notes

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