Dimethylamine → HCID 16071142, compound

HRID 2240023Notes

Reaction equation

HRID 2240023 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH2:12][CH2:13]OS(C3C=CC(C)=CC=3)(=O)=O)=[CH:8][CH:9]=2)[C:4]([S:25]([C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=[CH:30][CH:29]=2)(=[O:27])=[O:26])=[N:3]1.C1COCC1.[CH3:43][NH:44][CH3:45]>>[CH3:43][N:44]([CH3:45])[CH2:13][CH2:12][O:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:2]([CH3:1])[N:3]=[C:4]2[S:25]([C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=1)(=[O:27])=[O:26]

Participants

4

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 58812060HCID 58812060, compound

Product 1

HCID 16071142HCID 16071142, compound

Procedure

A solution of toluene-4-sulfonic acid 2-[1-methyl-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl ester (0.39 g, 0.73 mmol) in 2.0 M dimethylamine in THF (10 mL, 20 mmol) was stirred for 16.5 hours at 80° C. in a sealed tube. After cooling to ambient temperature, the reaction mixture was solvent evaporated. The residue was partitioned in ethyl acetate and aqueous sodium bicarbonate. The organic phase was washed with brine, dried with anhydrous magnesium sulfate, filtered, concentrated and dried at 80° C. in vacuo for 35 minutes to give dimethyl-{2-[1-methyl-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl}-amine a light brown-orange semi-solid (0.257 g, 86.2%). This was dissolved in chloroform, and ethereal hydrochloride was added. The mixture was concentrated and dried for 25 hours at 83° C. in vacuo to give the hydrochloride as a buff-colored foam (0.254 g). Mass Spectrum (+EI, [M+H]+) m/z 410. 1HNMR (500 MHz, DMSO-d6): δ10.25 (s, 1H), 8.74-8.76 (m, 1H), 8.51 (dd, 1H, J=7.44 Hz and 1.22 Hz), 8.26-8.28 (m, 1H), 8.03-8.05 (m, 1H), 7.71-7.74 (m, 2H), 7.56-7.66 (m, 2H), 7.39 (d, 1H, J=2.08 Hz), 7.22 (dd, 1H, J=9.28 Hz and 2.32 Hz), 4.39-4.42 (m, 2H), 4.05 (s, 3H), 3.50-3.52 (m, 2H), 2.83 ppm (s, 6H).

Workup

  1. customevaporated
  2. customThe residue was partitioned in ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried at 80° C. in vacuo for 35 minutes

Sources & evidence

ORD record
ord-9df0147fc0dc4d8a82a28fbc90a3bdd5
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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