Ammonium Chloride → HCID 70663234, compound

HRID 878286Notes

Reaction equation

HRID 878286 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:14]([CH3:28])[C:15](=[O:27])[C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([SH:26])[CH:17]=2)=[C:4]([O:29][CH3:30])[CH:3]=1.I[CH:32]1[CH2:35][O:34][CH2:33]1.CCN(C(C)C)C(C)C.[NH4+].[Cl-]>C(#N)C.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:14]([CH3:28])[C:15](=[O:27])[C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([S:26][CH:32]3[CH2:35][O:34][CH2:33]3)[CH:17]=2)=[C:4]([O:29][CH3:30])[CH:3]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 133566863-IodooxetaneHCID 70663556HCID 70663556, compound

Product 1

HCID 70663234HCID 70663234, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(4-(4-fluoro-2-methoxyphenyl)pyridin-3-yl)-3-mercapto-N-methyl-5-(trifluoromethyl)benzamide (0.1 g, 229 μmol, example 129, intermediate) in acetonitrile (2 mL) were added 3-iodooxetane (52.7 mg, 286 μmol, CAS RN 26272-85-5) and DIPEA (74.0 mg, 100 μL, 573 μmol) and the yellow solution was stirred at room temperature for 1.5 hours. Then heating was installed and the yellow solution was stirred at reflux for 2.5 hours. The colorless solution was poured on saturated aqueous NH4Cl solution and EtOAc and the layers were separated. The aqueous layer was extracted twice with EtOAc. The organic layers were dried over MgSO4, filtered, and evaporated. The compound was purified by silica gel chromatography on a 10 g column using an MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Light brown foam (0.052 g; 46%). MS (ESI): m/z=493.12 [M+H]+.

Workup

  1. temperatureThen heating
  2. stirringthe yellow solution was stirred
  3. temperatureat reflux for 2.5 hours
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted twice with EtOAc
  6. dry with materialThe organic layers were dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe compound was purified by silica gel chromatography on a 10 g column
  10. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

Sources & evidence

ORD record
ord-59e74c995cd84b1c946dc66711c27820
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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