Water → HCID 56836905, compound

HRID 591187Notes

Reaction equation

HRID 591187 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:20]([C:22]3[CH:23]=[C:24]([CH:35]=[CH:36][CH:37]=3)[O:25][CH2:26][CH2:27][NH:28][S:29]([CH2:32][CH2:33][CH3:34])(=[O:31])=[O:30])=O)[CH2:19][CH2:18][CH2:17]2)=[CH:12][CH:11]=1.C(O)(C)C.O>C(OC(=O)C)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH2:1]([NH:8][CH:20]([C:16]1([C:13]2[CH:14]=[CH:15][C:10]([Cl:9])=[CH:11][CH:12]=2)[CH2:19][CH2:18][CH2:17]1)[C:22]1[CH:23]=[C:24]([CH:35]=[CH:36][CH:37]=1)[O:25][CH2:26][CH2:27][NH:28][S:29]([CH2:32][CH2:33][CH3:34])(=[O:31])=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 7504BenzylamineHCID 66747244HCID 66747244, compound

Product 1

HCID 56836905HCID 56836905, compoundYield 9.8%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
35 °C

Procedure

Titanium (IV) isopropoxide (235 mg, 0.83 mmol) was added under nitrogen at room temperature to a mixture of benzylamine (147 mg, 1.37 mmol) and propane-1-sulfonic acid (2-{3-[1-(4-chloro-phenyl)-cyclobutanecarbonyl]-phenoxy}-ethyl)-amide (120 mg, 0.27 mmol), followed by 1 ml of isopropanol. The mixture was stirred at 35° C. for 6 h, then over night at room temperature followed by addition of NaCNBH4 (43 mg, 0.69 mmol) and heating to reflux for further 6 hours. The suspension was treated with water and diluted with ethylacetate and filtered. The organic layer was separated, washed with water, dried (sodium sulfate) and the solvent evaporated. Purification on SiO2 afforded 14 mg of desired product which was further purified by transformation into the hydrochloride. (white solid, 2.7 mg)

Workup

  1. additionover night at room temperature followed by addition of NaCNBH4 (43 mg, 0.69 mmol)
  2. temperatureheating
  3. temperatureto reflux for further 6 hours
  4. filtrationfiltered
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materialdried (sodium sulfate)
  8. customthe solvent evaporated
  9. customPurification on SiO2

Sources & evidence

ORD record
ord-d51276389e9f44bb96475ce61ec73b03
Source dataset
uspto-grants-2016_01
Patent number
US09238619B2

Reaction notes

Loading…