tert-Butanol → HCID 86759316, compound

HRID 1838269Notes

Reaction equation

HRID 1838269 reaction equation
C(O)(C)(C)C.[C:6]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C@H:19]([CH3:20])[CH2:18][N:17]([C:21]([NH:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26](C(O)=O)[CH:25]=3)=[O:22])[C@@H:16]([CH3:33])[CH2:15]2)=[CH:10][C:9]=1[C:34]([F:37])([F:36])[F:35])#[N:7].C1C=CC(P([N:52]=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1>C(N(CC)CC)C>[NH2:52][C:26]1[CH:25]=[C:24]([NH:23][C:21]([N:17]2[CH2:18][C@@H:19]([CH3:20])[N:14]([C:11]3[CH:12]=[CH:13][C:8]([C:6]#[N:7])=[C:9]([C:34]([F:35])([F:37])[F:36])[CH:10]=3)[CH2:15][C@@H:16]2[CH3:33])=[O:22])[CH:29]=[CH:28][N:27]=1

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 199401P,P-Diphenylphosphinic azideHCID 86759317HCID 86759317, compound

Product 1

HCID 86759316HCID 86759316, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A 50 ml portion of t-butanol solution containing 1.38 g of (+/−)-trans-4-{[4-(4-cyano-3-trifluoromethylphenyl)-2,5-dimethylpiperazine-1-carbonyl]amino}pyridine-2-carboxylic acid synthesized in the same manner as described in Example 12-1, 1.5 ml of DPPA and 1.5 ml of triethylamine was heated under reflux for 8 hours, and then the solvent was evaporated under reduced pressure. This was mixed with 30 ml of trifluoroacetic acid and stirred at room temperature for 1 hour, the solvent was evaporated under reduced pressure, and then the resulting residue was alkalified with saturated sodium bicarbonate solution. Next, this was extracted with ethyl acetate, the organic layer was washed with purified water and then with saturated brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by a silica gel column chromatography to obtain 0.94 g of the title compound from chloroform-methanol (10:1, v/v) eluate. Thereafter, this was crystallized from ethyl acetate-hexane to obtain 0.72 g of the title compound as white crystals.

Workup

  1. customsynthesized in the same manner
  2. temperaturewas heated
  3. temperatureunder reflux for 8 hours
  4. customthe solvent was evaporated under reduced pressure
  5. additionThis was mixed with 30 ml of trifluoroacetic acid
  6. customthe solvent was evaporated under reduced pressure
  7. extractionNext, this was extracted with ethyl acetate
  8. washthe organic layer was washed with purified water
  9. dry with materialwith saturated brine and dried over anhydrous sodium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. customThe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-1e411c921c164f09bb445f1abc51b127
Source dataset
uspto-grants-2004_01
Patent number
US06673799B1

Reaction notes

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