Sodium Azide → HCID 178521662, compound

HRID 1965970Notes

Reaction equation

HRID 1965970 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1[C:19]#[C:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[N-:27]=[N+:28]=[N-:29].[Na+]>CS(C)=O.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:14])([F:13])[F:15])[CH2:9][CH2:10][C:4]=2[C:3]=1[C:19]1[NH:27][N:28]=[N:29][C:20]=1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 59787350HCID 59787350, compound

Product 1

HCID 178521662HCID 178521662, compoundYield 39.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Heat 7-chloro-6-phenylethynyl-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (100 mg, 0.26 mmol) and sodium azide (69 mg, 1.06 mmol) in anhydrous DMSO (5.3 mL) for 5.5 h. Cool the mixture, add brine and extract ten times with dichloromethane. Dry the combined organic extracts over Na2SO4, filter and evaporate onto silica gel. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0 to 2:3 gradient) to obtain the desired intermediate (43 mg, 39%). MS (ES+) m/z: 421 (M+H)+.

Workup

  1. temperatureCool the mixture
  2. extractionextract ten times with dichloromethane
  3. dry with materialDry the combined organic extracts over Na2SO4
  4. filtrationfilter
  5. customevaporate onto silica gel
  6. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0 to 2:3 gradient)

Sources & evidence

ORD record
ord-89d93e4eca0d4593b727c9741e288361
Source dataset
uspto-grants-2013_04
Patent number
US08420631B2

Reaction notes

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