Dimethylamine → HCID 178483562, compound

HRID 2240004Notes

Reaction equation

HRID 2240004 reaction equation
[C:1]1([S:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH2:24][CH2:25][CH2:26]OS(C4C=CC(C)=CC=4)(=O)=O)[CH:21]=3)[NH:16][N:15]=2)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C1COCC1.[CH3:43][NH:44][CH3:45]>>[CH3:43][N:44]([CH3:45])[CH2:26][CH2:25][CH2:24][O:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[NH:16][N:15]=[C:14]2[S:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)(=[O:12])=[O:13]

Participants

4

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 178427737HCID 178427737, compound

Product 1

HCID 178483562HCID 178483562, compound

Procedure

A solution of toluene-4-sulfonic acid 3-[3-(naphthalene-1-sulfonyl)-1H-indazol -5-yloxy]-propyl ester (1.02 g, 1.89 mmol) in 2.0 M dimethylamine in THF (20 mL, 40 mmol) was stirred for 16 hours at 70° C. in a sealed tube. After cooling to ambient temperature, the reaction mixture was concentrated and partitioned in chloroform and aqueous sodium bicarbonate. The organic phase was washed with brine, dried with anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography using 0.5% ammonium hydroxide/5.0% methanol in chloroform. Dimethyl-{3-[3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-propyl}-amine was obtained as a light yellow solid (0.453 g, 58.5%). Methanol and ethereal hydrochloride were then added to this compound. The resulting solution was concentrated and dried for 14 hours at 84° C. in vacuo. Dimethyl-{3-[3-(naphthalene -1-sulfonyl)-1H-indazol-5-yloxy]-propyl}-amine hydrochloride as a very light yellow solid (0.455 g) was obtained: MP: 264-5° C.; Mass Spectrum (−EI, [M−H]−) m/z 408.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompartitioned in chloroform
  3. washThe organic phase was washed with brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-aa98296f66724f8e84c12eb2de7f8c47
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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