Sulfuric Acid → HCID 178424631, compound

HRID 456017Notes

Reaction equation

HRID 456017 reaction equation
[CH3:1][C:2]1([CH3:34])[CH2:7][CH2:6][C:5]([C:8]2[C:13]([NH:14][C:15]([C:17]3[NH:18][CH:19]=[C:20]([C:22]#[N:23])[N:21]=3)=[O:16])=[CH:12][CH:11]=[C:10]([CH:24]3[CH2:29][C:28]([CH3:31])([CH3:30])[O:27][C:26]([CH3:33])([CH3:32])[CH2:25]3)[N:9]=2)=[CH:4][CH2:3]1.[S:35](=[O:39])(=[O:38])([OH:37])[OH:36]>C(#N)C.O>[S:35]([OH:39])([OH:38])(=[O:37])=[O:36].[CH3:1][C:2]1([CH3:34])[CH2:7][CH2:6][C:5]([C:8]2[C:13]([NH:14][C:15]([C:17]3[NH:18][CH:19]=[C:20]([C:22]#[N:23])[N:21]=3)=[O:16])=[CH:12][CH:11]=[C:10]([CH:24]3[CH2:25][C:26]([CH3:33])([CH3:32])[O:27][C:28]([CH3:31])([CH3:30])[CH2:29]3)[N:9]=2)=[CH:4][CH2:3]1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 178424627HCID 178424627, compound

Product 1

HCID 178424631HCID 178424631, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A suspension of 4-cyano-1H-imidazole-2-carboxylic acid[2-(4,4-dimethyl-cyclohex-1-enyl)-6-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-yl]-amide (24.8 mg, 0.0537 mmol), as prepared in Example 15, in acetonitrile (1.0 mL) was heated to yield a solution. To the solution was added a solution of concentrated sulfuric acid (0.0062 mL) in water (0.5 mL) at room temperature. The solution was reduced via evaporation with flowing nitrogen gas (approximately 1.0 mL). The solution was then allowed to sit overnight at room temperature in a sealed vial. The resulting crystals were then collected via filtration and air-dried. The white solid was characterized by Powder X-Ray Diffraction (PXRD), Differential Scanning Calorimetry (DSC), Thremogravimetric Analysis (TGA), and single-crystal X-ray diffraction. The DSC for the sulfate salt showed a 241 degree Celsius endotherm maximum. The PXRD of the sulfate salt product is shown in FIG. 1 and the prominent peaks are shown in the table below.

Workup

  1. temperaturewas heated
  2. customto yield a solution
  3. customThe solution was reduced via evaporation with flowing nitrogen gas (approximately 1.0 mL)
  4. filtrationThe resulting crystals were then collected via filtration
  5. customair-dried
  6. customshowed a 241 degree Celsius

Sources & evidence

ORD record
ord-a98d1a652046417faeb0ef8be45de9f9
Source dataset
uspto-grants-2013_07
Patent number
US08497376B2

Reaction notes

Loading…