Sodium Azide → HCID 59596383, compound

HRID 2264579Notes

Reaction equation

HRID 2264579 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]3[CH:19]=[C:20]([O:23][C:24]4[CH:29]=[C:28](Cl)[N:27]=[CH:26][N:25]=4)[CH:21]=[CH:22][C:13]2=3)=[O:11])[CH:6]=[CH:7][CH:8]=1.[N-:33]=[N+:34]=[N-:35].[Na+]>CN(C=O)C.CCOC(C)=O.O>[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]3[CH:19]=[C:20]([O:23][C:24]4[CH:29]=[C:28]([N:33]=[N+:34]=[N-:35])[N:27]=[CH:26][N:25]=4)[CH:21]=[CH:22][C:13]2=3)=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 11503607HCID 11503607, compound

Product 1

HCID 59596383HCID 59596383, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 300 mg (0.65 mMol) of 7-(6-chloro-pyrimidin-4-yloxy)-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide and 84 mg (1.3 mMol) NaN3 in 3.8 ml DMF is stirred at 60° C. for 90 min. Then the solution is diluted with EtOAc and water, the aqueous layer separated off and extracted twice with EtOAc. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated, yielding the title compound: MS: [M+1]+=470; HPLC: AtRet=16.9.

Workup

  1. customthe aqueous layer separated off
  2. extractionextracted twice with EtOAc
  3. washThe organic phases are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-01616cb141e04094bf8a5e4f9b5e84ae
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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