Acetic Acid → HCID 24957692, compound

HRID 1097788Notes

Reaction equation

HRID 1097788 reaction equation
CC(O)=O.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C([SiH2][O:28][C:29](C1C=CC=CC=1)(C1C=CC=CC=1)[C:30]1[N:34]([CH:35]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[N:38]([C:45](=[O:53])[CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[CH2:37][C:36]2([CH3:55])[CH3:54])[CH:33]=[N:32][CH:31]=1)(C)(C)C.C([O-])(O)=O.[Na+]>C1COCC1>[OH:28][CH2:29][C:30]1[N:34]([CH:35]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[N:38]([C:45](=[O:53])[CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[CH2:37][C:36]2([CH3:55])[CH3:54])[CH:33]=[N:32][CH:31]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium Fluoride2×HCID 131729531HCID 131729531, compound

Product 1

HCID 24957692HCID 24957692, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

HOAc (0.05 mL, 0.88 mmol) and TBAF (0.3 mL, 0.37 mmol) are added to a solution of 1-{4-[5-(tert-butyl-diphenyl-silanyloxymethyl)-imidazol-1-yl]-3,3-dimethyl-3,4-dihydro-2H-quinolin-1-yl}-2-phenyl-ethanone (115 mg) in THF (6 mL) at room temperature. The mixture is stirred at room temperature. In the next 4 h, TBAF (0.3 mL×2) are added and the mixture is stirred at room temperature for overnight. The reaction is adjusted by sat. NaHCO3 to basic and extracted into ethyl acetate and washed with brine; dried with anhydrous sodium sulfate and concentrated to give the crude compound, which is purified by reverse phase HPLC (CH3CN:H2O=10 to 80% over 20 mins) to the title compound: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.73 (s, 3 H), 0.97 (s, 3 H), 3.53 (br. s., 1H), 3.65 (d, J=13.1 Hz, 1 H), 3.83 (d, J=13.1 Hz, 1 H), 4.00 (s, 2 H), 4.70 (dd, 2 H), 5.30 (s, 1 H), 6.89-6.95 (m, 2 H), 7.03 (t, J=7.5 Hz, 1 H), 7.10 (s, 1 H), 7.24-7.37 (m, 6 H), 7.61 (br. s., 1 H).

Workup

  1. stirringthe mixture is stirred at room temperature for overnight
  2. extractionextracted into ethyl acetate
  3. washwashed with brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-51598fca68544e86962905f307da4d48
Source dataset
uspto-grants-2012_03
Patent number
US08143278B2

Reaction notes

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