Potassium Carbonate → HCID 17973671, compound

HRID 2077371Notes

Reaction equation

HRID 2077371 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][C:15](O)=O)=O)(C)(C)C.[F:18][C:19]1[CH:20]=[C:21]([NH2:27])[C:22]([NH2:26])=[CH:23][C:24]=1[F:25].C(=O)([O-])[O-].[K+].[K+]>>[F:18][C:19]1[C:24]([F:25])=[CH:23][C:22]2[NH:26][C:15]([CH2:14][CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][NH:8]3)=[N:27][C:21]=2[CH:20]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 27367551,2-Diamino-4,5-difluorobenzeneHCID 50585361-Boc-2-Piperidineacetic Acid

Product 1

HCID 17973671HCID 17973671, compoundYield 69.3%

Conditions

Temperature
140 °C

Procedure

A mixture of 2-carboxymethyl-piperidine-1-carboxylic acid tert-butyl ester (Beckett et al, J. Med. Chem., 563, 1969) (10.0 g, 41 mmol) and 4,5-difluoro-benzene-1,2-diamine (5.95 g, 41 mmol) in polyphosphoric acid (140 g) was heated at 140° C. for 7 h. The cooled reaction mixture was poured onto excess solid potassium carbonate and crushed ice. The resulting basic, aqueous solution was extracted with ethyl acetate (2×) and the combined organics were washed with brine, dried (Na2SO4) and the solvent removed in vacuo. The residue was triturated with diethyl ether, ethyl acetate and pentane to afford the title compound as a light brown solid (7.14 g, 69%).

Workup

  1. customThe cooled reaction mixture
  2. customcrushed ice
  3. extractionThe resulting basic, aqueous solution was extracted with ethyl acetate (2×)
  4. washthe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customthe solvent removed in vacuo
  7. customThe residue was triturated with diethyl ether, ethyl acetate and pentane

Sources & evidence

ORD record
ord-d78882f6911449768019b28767293040
Source dataset
uspto-grants-2011_04
Patent number
US07928125B2

Reaction notes

Loading…