Sodium Azide → HCID 58659356, compound

HRID 1993568Notes

Reaction equation

HRID 1993568 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][N:26]4[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]4)=[C:21]([C:32]([F:35])([F:34])[F:33])[CH:20]=3)=[O:17])=[CH:11][CH:10]=2)[N:5]=[CH:4][N:3]=1.[N-:36]=[N+:37]=[N-:38].[Na+]>CN(C=O)C>[N:36]([C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][N:26]4[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]4)=[C:21]([C:32]([F:35])([F:34])[F:33])[CH:20]=3)=[O:17])=[CH:11][CH:10]=2)[N:5]=[CH:4][N:3]=1)=[N+:37]=[N-:38]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 58659422HCID 58659422, compound

Product 1

HCID 58659356HCID 58659356, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of N-(4-(4-chloropyrimidin-6-yl-oxy)-phenyl)-N′-(3-trifluoromethyl-4-(piperidin-1-ylmethyl)-phenyl)-urea (Example 128; 350 mg, 0.69 mmol) and NaN3 (91 mg, 1.4 mmol) in 7 ml of DMF is stirred for 2 h at 70° C. The resulting mixture is concentrated in vacuo, the residue diluted with AcOEt and water, the aqueous layer separated off and extracted twice with AcOEt. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated to yield the title compound: MS: [M+1]+=513.

Workup

  1. concentrationThe resulting mixture is concentrated in vacuo
  2. additionthe residue diluted with AcOEt and water
  3. customthe aqueous layer separated off
  4. extractionextracted twice with AcOEt
  5. washThe organic phases are washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-79c9074d9054428796011f93b203051a
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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