Dimethylformamide → HCID 44467337, compound

HRID 1798836Notes

Reaction equation

HRID 1798836 reaction equation
[H-].[Na+].CN(C=O)C.[Cl:8][C:9]1[CH:10]=[N:11][C:12]([N:15]2[CH2:20][CH2:19][CH:18]([C@@H:21]3[CH2:23][C@H:22]3[CH2:24][CH2:25][OH:26])[CH2:17][CH2:16]2)=[N:13][CH:14]=1.[Cl-].F[C:29]1[CH:34]=[CH:33][NH+:32]=[CH:31][CH:30]=1>C(OCC)(=O)C>[Cl:8][C:9]1[CH:10]=[N:11][C:12]([N:15]2[CH2:20][CH2:19][CH:18]([C@@H:21]3[CH2:23][C@H:22]3[CH2:24][CH2:25][O:26][C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)[CH2:17][CH2:16]2)=[N:13][CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 66934999HCID 66934999, compoundHCID 66935352HCID 66935352, compound

Product 1

HCID 44467337HCID 44467337, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (100%, 20 mg, 0.85 mmol) was weighed into a vial, DMF (anhydrous, 2.1 mL) was added, followed by addition of rac-trans 2-{2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethanol (60 mg, 0.21 mmol) and the mixture stirred at room temperature for 5 min. The 4-fluoropyridinium chloride was then added and stirred at room temperature for 10 min. The mixture was heated to 50° C. for 1.5 hours, cooled to room temperature, and diluted with ethyl acetate (5 mL), quenched with saturated aq.NH4Cl (5 mL), dried over MgSO4, filtered and concentrated. The crude residue was purified by silica gel chromatography (30% ethyl acetate/hexane) to yield the titled compound as a white solid. LC-MS (M+1): 359.54. Compounds Reported in Table 3 are Prepared by a General Procedure Analogous to that Described in Example 6, Steps 1 and 2, Described Above

Workup

  1. additionwas added
  2. stirringstirred at room temperature for 10 min
  3. temperatureThe mixture was heated to 50° C. for 1.5 hours
  4. temperaturecooled to room temperature
  5. customquenched with saturated aq
  6. dry with materialNH4Cl (5 mL), dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude residue was purified by silica gel chromatography (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-dedd91c084f944debf98866e015084fd
Source dataset
uspto-grants-2013_01
Patent number
US08343990B2

Reaction notes

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