Sodium Azide → HCID 86613525, compound

HRID 1441327Notes

Reaction equation

HRID 1441327 reaction equation
CS(O[CH:6]1[CH2:9][N:8]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[N:22]=[C:21]([C:23]4[N:27]([CH:28]([CH3:30])[CH3:29])[C:26]([CH3:31])=[N:25][CH:24]=4)[C:20]([F:32])=[CH:19][N:18]=3)=[CH:12][CH:11]=2)[CH2:7]1)(=O)=O.[N-:33]=[N+:34]=[N-:35].[Na+]>CN(C=O)C.CCOC(C)=O>[N:33]([CH:6]1[CH2:9][N:8]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[N:22]=[C:21]([C:23]4[N:27]([CH:28]([CH3:30])[CH3:29])[C:26]([CH3:31])=[N:25][CH:24]=4)[C:20]([F:32])=[CH:19][N:18]=3)=[CH:12][CH:11]=2)[CH2:7]1)=[N+:34]=[N-:35]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86613524HCID 86613524, compound

Product 1

HCID 86613525HCID 86613525, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-(4-{[5-fluoro-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidin-2-yl]amino}phenyl)azetidin-3-yl methanesulfonate (Example 138; 876 mg, 1.90 mM) in dry DMF (7.3 ml), sodium azide (619 mg, 9.5 mM) was added. The reaction was stirred and heated at 80° C. under nitrogen for 18 hours. The reaction mixture was diluted with EtOAc and the solution extracted with water (twice), saturated sodium chloride and then dried with anhydrous sodium sulphate filtered and evaporated. The crude product was purified by silica chromatography eluting with MeOH:DCM (2:98) to give the title compound as a brown foam (389 mg, 50%). NMR 1.4 (d, 6H), 2.53 (s, 3H+DMSO), 3.65 (m, 2H), 4.1 (m, 2H), 4.44 (m, 1H), 5.4 (m, 1H), 6.44 (d, 2H), 7.33 (m, 3H), 8.35 (d, 1H); m/z 408.

Workup

  1. extractionthe solution extracted with water (twice), saturated sodium chloride
  2. dry with materialdried with anhydrous sodium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified by silica chromatography
  6. washeluting with MeOH:DCM (2:98)

Sources & evidence

ORD record
ord-30152fd09a904502b47e084d2dfa8e08
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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