Tetrahydrofuran → HCID 59774844, compound

HRID 2387284Notes

Reaction equation

HRID 2387284 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]3[C:15](CC(C4C=C5C(C=CN5S(CCC)(=O)=O)=CC=4)=O)=[CH:14][NH:13][C:10]3=[N:11][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[F-].C([N+:39]([CH2:48][CH2:49][CH2:50][CH3:51])([CH2:44][CH2:45][CH2:46][CH3:47])CCCC)CCC.[O:52]1CCC[CH2:53]1>>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]3[C:15]([C:53]([C:46]4[CH:45]=[C:44]5[C:50]([CH:49]=[CH:48][NH:39]5)=[CH:51][CH:47]=4)=[O:52])=[CH:14][NH:13][C:10]3=[N:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 2724141Tetrabutylammonium FluorideHCID 69236933HCID 69236933, compound

Product 1

HCID 59774844HCID 59774844, compound

Conditions

Temperature
60 °C

Procedure

To (5-Cyclopentyloxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1-(propane-1-sulfonyl)-1H-indol-6-yl]-methanone (62, 0.065 g, 0.14 mmol) dissolved in tetrahydrofuran (5.10 mL, 0.0628 mol), 1.00 M tetra-n-butylammonium fluoride in tetrahydrofuran (0.475 mL) was added. The resulting solution was allowed to stir at 60° C. under an atmosphere of nitrogen. After 19 hours, the reaction was quenched with water, and the two layers were separated. The organic layer was extracted with 50% sat. NaHCO3 (in water), followed by sat. bicarbonate, 1N HCl, and brine. The organic layer was dried with anhydrous magnesium sulfate and filtered. The filtrate was concentrated and purified by HPLC to give 1.7 mg of compound P-0040. MS (ESI) [M+H+]+=346.2.

Workup

  1. customthe reaction was quenched with water
  2. customthe two layers were separated
  3. extractionThe organic layer was extracted with 50% sat. NaHCO3 (in water)
  4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified by HPLC

Sources & evidence

ORD record
ord-b1f464b2276f4c279b5036824d97b6cd
Source dataset
uspto-grants-2012_09
Patent number
US08268858B2

Reaction notes

Loading…