Acetic Acid → HCID 21877436, compound

HRID 724446Notes

Reaction equation

HRID 724446 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1/[CH:7]=[CH:8]/[C:9]1[C:17]2[C:12](=[CH:13][C:14]([C:18]([C:20]3[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=3[C:22]([OH:24])=[O:23])=[O:19])=[CH:15][CH:16]=2)[N:11](COCC[Si](C)(C)C)[N:10]=1.C(N)CN.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1.C(O)(=O)C>C(OCC)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1/[CH:7]=[CH:8]/[C:9]1[C:17]2[C:12](=[CH:13][C:14]([C:18]([C:20]3[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=3[C:22]([OH:24])=[O:23])=[O:19])=[CH:15][CH:16]=2)[NH:11][N:10]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 3301EthylenediamineHCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 21877257HCID 21877257, compound

Product 1

HCID 21877436HCID 21877436, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-{1-[3-((E)-2-Pyridin-2-yl-vinyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-6-yl]-methanoyl}-benzoic acid (402 mg, 0.805 mmol) (synthesis described below), ethylene diamine (215 μL, 3.22 mmol), and 1M TBAF in THF (6.44 ml, 6.44 mmol), was stirred in a 90° C. oil bath for 4 hr. The crude reaction mixture was quenched with acetic acid (386 μL, 6.44 mmol), diluted with ethyl acetate (100 mL), extracted 1M sodium bicarbonate solution (2×20 ml), brine (5×20 ml), dried magnesium sulfate, filtered, and concentrated to a 3 mL volume. The resulting crude material was purified by preparative C18 reverse phase column chromatography, giving 211 mg of the title compound as a yellow solid (71% yield). 1H NMR (DMSO-d6) δ 13.50 (bs, 1H), 8.68 (d, J=5.27 Hz, 1H), 8.29 (d, J=8.86 Hz, 1H), 8.13–7.90 (m, 4H), 7.81–7.43 (m, 7H).

Workup

  1. customThe crude reaction mixture
  2. extractionextracted 1M sodium bicarbonate solution (2×20 ml), brine (5×20 ml), dried magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to a 3 mL volume
  5. customThe resulting crude material was purified by preparative C18 reverse phase column chromatography

Sources & evidence

ORD record
ord-1fcce158d3bf462e85f65b006de45214
Source dataset
uspto-grants-2006_11
Patent number
US07141587B2

Reaction notes

Loading…