Triethylamine → HCID 178513847, compound

HRID 1960068Notes

Reaction equation

HRID 1960068 reaction equation
C(N(CC)CC)C.[F:8][C:9]([F:27])([F:26])[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17](=[O:25])OC2C=CC=CC=2)[CH:11]=1.[NH2:28][C:29]1[CH:30]=[C:31]([CH:42]=[CH:43][CH:44]=1)[CH2:32][NH:33][C:34]1[C:35]([C:39]([NH2:41])=[O:40])=[N:36][NH:37][CH:38]=1>C1COCC1.C(OCC)(=O)C>[F:27][C:9]([F:8])([F:26])[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17](=[O:25])[NH:28][C:29]2[CH:30]=[C:31]([CH:42]=[CH:43][CH:44]=2)[CH2:32][NH:33][C:34]2[C:35]([C:39]([NH2:41])=[O:40])=[N:36][NH:37][CH:38]=2)[CH:11]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 57955188Phenyl (4-(trifluoromethyl)pyridin-2-yl)carbamateHCID 178513846HCID 178513846, compound

Product 1

HCID 178513847HCID 178513847, compoundYield 27.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

88 μl of triethylamine and 0.18 g of phenyl (4-trifluoromethylpyrid-2-yl)carbamate are added at 20° C. to a solution of 0.12 g of 4-(3-aminobenzylamino)-1H-pyrazole-3-carboxamide in 5 ml of anhydrous THF. The reaction medium is heated in a microwave reactor for 20 minutes and, after cooling, is diluted with 25 ml of ethyl acetate. The organic phase is washed with twice 15 ml of distilled water and then separated out by settling of the phases, dried over magnesium sulfate and evaporated to dryness under reduced pressure. The residue obtained is chromatographed on a column of silica (15 g of Merck cartridge silica with a particle size of 15 to 45 μm, column diameter 2.2 cm, 3.5 ml fractions, flow rate of 7 ml/min, ethyl acetate eluent). Fractions 36 to 60 are combined and evaporated to dryness under reduced pressure. 0.06 g of 4-{3-[3-(4-trifluoromethylpyrid-2-yl)ureido]benzylamino}-1H-pyrazole-3-carboxamide is obtained in the form of a white solid. ([M+H]+): 420). RT: 0.78 min (Method D).

Workup

  1. temperatureThe reaction medium is heated in a microwave reactor for 20 minutes
  2. temperatureafter cooling
  3. washThe organic phase is washed with twice 15 ml of distilled water
  4. customseparated out
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customThe residue obtained
  8. customis chromatographed on a column of silica (15 g of Merck cartridge silica with a particle size of 15 to 45 μm, column diameter 2.2 cm, 3.5 ml fractions, flow rate of 7 ml/min, ethyl acetate eluent)
  9. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-02bbc02489ca4313b28761635a6bb53b
Source dataset
uspto-grants-2013_04
Patent number
US08410286B2

Reaction notes

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