Dimethylamine → HCID 178483859, compound

HRID 2240018Notes

Reaction equation

HRID 2240018 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]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.[CH3:42][NH:43][CH3:44]>>[CH3:42][N:43]([CH3:44])[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:13])=[O:12]

Participants

4

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 178427773HCID 178427773, compound

Product 1

HCID 178483859HCID 178483859, compoundYield 73.4%

Procedure

A solution of toluene-4-sulfonic acid 2-[3-(naphthalene-1-sulfonyl)-1H-indazol -5-yloxy]-ethyl ester (0.382 g, 0.731 mmol) in 2.0 M dimethylamine in THF (8 mL, 16 mmol) was stirred for 4 hours at 70° C. in a sealed tube. After cooling to ambient temperature, the reaction mixture was concentrated and partitioned in ethyl acetate and aqueous sodium bicarbonate. The organic phase was washed with water and brine, dried with anhydrous magnesium sulfate, filtered and concentrated. Drying at 80° C. for 20 minutes in vacuo yielded dimethyl-{2-[3-(naphthalene-1-sulfonyl)-1H-indazol -5-yloxy]-ethyl}-amine as a light yellow solid (0.212 g, 73.4%). Methanol, chloroform and etheric hydrochloride were added. The resulting solution was concentrated and dried for 15 hours at 78° C. in vacuo. The hydrochloride as a buff foam (0.217 g) was obtained. Mass Spectrum (+EI, [M+H]+) m/z 396. 1HNMR (500 MHz, DMSO-d6): δ14.20 (s, 1H), 10.05 (s, 1H), 8.74-8.77 (m, 1H), 8.52 (dd, 1H, J=7.44 Hz and 1.22 Hz), 8.27 (d, 1H, J=8.17 Hz), 8.03-8.05 (m, 1H), 7.70-7.74 (m, 1H), 7.56-7.65 (m, 3H), 7.37 (d, 1H, J=2.20 Hz), 7.15-7.18 (m, 1H), 4.37-4.39 (m, 2H), 3.51 (t, 2H, J=4.76 Hz), 2.83 ppm (s, 6H). Elemental Analysis for C21H21N3O3S.1.00 mol HCl.0.70 mol H2O: Calcd: C, 56.74; H, 5.31; N, 9.45; Found: C, 56.72; H, 5.33; N, 9.06.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompartitioned in ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customDrying at 80° C. for 20 minutes in vacuo

Sources & evidence

ORD record
ord-e319e3dc33804b7294599620559d92a6
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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