Dimethyl Sulfoxide → HCID 178453635, compound

HRID 1963855Notes

Reaction equation

HRID 1963855 reaction equation
[Cl:1][C:2]1[C:3]([I:9])=[CH:4][C:5](F)=[N:6][CH:7]=1.[NH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:13][CH2:12]1.CS(C)=O>C(OCC)(=O)C>[C:21]([O:20][C:19](=[O:25])[NH:18][CH2:17][C@H:14]1[CH2:13][CH2:12][C@H:11]([NH:10][C:5]2[CH:4]=[C:3]([I:9])[C:2]([Cl:1])=[CH:7][N:6]=2)[CH2:16][CH2:15]1)([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 218653365-Chloro-2-fluoro-4-iodopyridineHCID 178453642HCID 178453642, compound

Product 1

HCID 178453635HCID 178453635, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 5-chloro-2-fluoro-4-iodopyridine (517 mg, 2.008 mmol), tert-butyl (trans-4-aminocyclohexyl)methylcarbamate (550 mg, 2.410 mmol), DMSO (2 ml) and TEA (0.336 ml, 2.410 mmol) reaction mixture was stirred at about 95° C. for about 26 hours. The crude reaction mixture mixture was cooled to room temperature, mixed with 125 ml ethyl acetate, washed with saturated sodium bicarbonate (2×), water (3×), saturated salt solution (1×), dried sodium sulfate, filtered and concentrated under reduced pressure to yield a residue. The residue was purified by silica gel chromatography using a 40 g column, eluting from 0%-35% ethyl acetate with hexane. The desired fractions were concentrated to constant mass, yielding 656 mg of titled compound as free base. LCMS (m/z): 466.1 (MH+), retention time=0.93 min.

Workup

  1. customThe crude reaction mixture mixture
  2. temperaturewas cooled to room temperature
  3. washwashed with saturated sodium bicarbonate (2×), water (3×), saturated salt solution (1×), dried sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto yield a residue
  7. customThe residue was purified by silica gel chromatography
  8. washeluting from 0%-35% ethyl acetate with hexane
  9. concentrationThe desired fractions were concentrated to constant mass

Sources & evidence

ORD record
ord-e4e820d12fb4423aa9f888b887e54e9f
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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