Potassium Carbonate → HCID 178525750, compound

HRID 2207344Notes

Reaction equation

HRID 2207344 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1.[Br:12][C:13]1[CH:14]=[CH:15][C:16](F)=[N:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([NH:2][C@H:3]2[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]2)=[N:17][CH:18]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 27831685-Bromo-2-fluoropyridineHCID 178479263HCID 178479263, compound

Product 1

HCID 178525750HCID 178525750, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of trans-4-aminocyclohexanecarboxylic acid hydrochloride (2.00 g, 11.1 mmol), 5-bromo-2-fluoropyridine (2.29 mL, 22.3 mmol), potassium carbonate (3.08 g, 22.3 mmol), DIEA (3.89 mL, 22.3 mmol) in NMP (50 mL) was heated to 130° C. overnight. The reaction was cooled to room temperature, filtered through a pad of CELITE, and washed with NMP (50 mL). The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography (CH2Cl2/MeOH, 0-10%) to afford trans-4-[(5-bromopyridin-2-yl)amino]cyclohexanecarboxylic acid as a off-white solid. MS ESI calc'd for C12H16BrN2O2 [M+H]+ 299 and 301. found 299 and 301.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered through a pad of CELITE
  3. washwashed with NMP (50 mL)
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (CH2Cl2/MeOH, 0-10%)

Sources & evidence

ORD record
ord-145167015416424091031172208670b1
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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