Ammonium Chloride → HCID 178490051, compound

HRID 1627255Notes

Reaction equation

HRID 1627255 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][S:11][C:12]2[N:13]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[C:14]([C:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([Cl:28])[CH:21]=3)([CH3:19])[CH3:18])=[CH:15][N:16]=2)=[CH:6][C:3]=1[C:4]#[N:5].[N-:36]=[N+:37]=[N-:38].[Na+].[NH4+].[Cl-]>CN(C=O)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][S:11][C:12]2[N:13]([C:29]3[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=3)[C:14]([C:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([Cl:28])[CH:21]=3)([CH3:18])[CH3:19])=[CH:15][N:16]=2)=[CH:6][C:3]=1[C:4]1[NH:38][N:37]=[N:36][N:5]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 667403762-Chloro-5-((5-(2-(3-chloro-4-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)benzonitrile

Product 1

HCID 178490051HCID 178490051, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-chloro-5-((5-(2-(3-chloro-4-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)benzonitrile (104 mg, 0.20 mmol), sodium azide (130 mg, 2.0 mmol, 10.0 eq) and NH4Cl (110 mg, 2.0 mmol) in DMF (2 mL, anhyd) was stirred at 110° C. for 16 h. The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The combined extracts were washed with water and brine, then dried over MgSO4 and concentrated. Purification by column chromatography (silica, 0 to 20% MeOH/DCM) provided the title compound (85 mg, 76%) as a white solid. 1H NMR (DMSO-d6, 400 MHz): δ 7.59 (d, J=1.7 Hz, 1H), 7.47 (d, J=8.3 Hz, 1H), 7.18-7.14 (m, 2H), 6.95-6.89 (m, 3H), 6.78-6.74 (m, 2H), 6.37-6.31 (m, 2H), 4.17 (s, 2H), 3.81 (s, 3H), 1.39 (s, 6H); MS (EI) m/z 569 (MH+).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between water and ethyl acetate
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customPurification by column chromatography (silica, 0 to 20% MeOH/DCM)

Sources & evidence

ORD record
ord-e5454270f2de4d7d9f048169711a7456
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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