Ammonium Chloride → HCID 178517580, compound

HRID 1972217Notes

Reaction equation

HRID 1972217 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=4)[CH2:16][N:15]([CH2:28][C:29]#[N:30])[C:14]3=[O:31])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[N-:34]=[N+:35]=[N-:36].[Na+].[NH4+].[Cl-]>CN(C=O)C>[NH:34]1[C:29]([CH2:28][N:15]2[CH2:16][CH:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:26])([F:25])[F:27])[CH:19]=3)[N:13]([C:10]3[CH:9]=[CH:8][C:7]([O:6][C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:33][CH:32]=4)=[CH:12][CH:11]=3)[C:14]2=[O:31])=[N:30][N:36]=[N:35]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 86645368HCID 86645368, compound

Product 1

HCID 178517580HCID 178517580, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
220 °C

Procedure

To a solution of 2-(3-(4-(4-chlorophenoxy)phenyl)-2-oxo-4-(3-(trifluoromethyl)phenyl)-imidazolidin-1-yl)acetonitrile (21.8 mg, 0.046 mmol) in DMF (1.0 mL) are added NaN3 (60 mg, 0.92 mmol) and NH4Cl (49 mg, 0.92 mmol). The reaction mixture is heated at 220° C. for 15 min in a microwave reactor. After cooling down to room temperature and removal of the solvent, the residue is purified by preparatory LC/MS to provide the title compound; 1H NMR (CDCl3, 400 MHz) δ 7.58-7.45 (m, 4H), 7.26 (d, 2H), 7.19 (d, 2H), 6.87 (m, 4H), 5.24 (dd, 1H), 4.95 (d, 1H), 4.69 (d, 1H), 4.10 (t, 1H), 3.48 (dd, 1H); HPLC-MS calculated for C24H18ClF3N6O2 (M+H+) 515.1, found 515.1.

Workup

  1. temperatureAfter cooling down to room temperature
  2. customremoval of the solvent
  3. customthe residue is purified by preparatory LC/MS

Sources & evidence

ORD record
ord-ac0aceef3f4941bbba3f297702288fb6
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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