Ethylamine → HCID 16071253, compound

HRID 2240026Notes

Reaction equation

HRID 2240026 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.[CH2:38]([NH2:40])[CH3:39]>C1COCC1>[CH2:38]([NH:40][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:26])=[O:27])[CH3:39]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 58812060HCID 58812060, compound

Product 1

HCID 16071253HCID 16071253, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of toluene-4-sulfonic acid 2-[1-methyl-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl ester (0.413 g, 0.770 mmol) and 2.0 M ethylamine in THF (10 mL, 20 mmol) in THF (10 mL) was stirred at 80° C. in a sealed tube for 16.5 hours. 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 20 minutes to give ethyl-{2-[1-methyl-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl}-amine as a dark yellow solid (0.292 g, 92.7%). This was dissolved in chloroform and methanol, 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 beige solid (0.227 g) MP 276-7° C.dec.; Mass Spectrum (+EI, [M+H]+) m/z 410. 1HNMR (500 MHz, DMSO-d6): δ8.95 (s, br, 2H), 8.75 (d, 1H, J=8.79 Hz), 8.52 (dd, 1H, J=7.45 Hz and 1.22 Hz), 8.27 (d, 1H, J=8.30 Hz), 8.04 (d, 1H, J=7.57 Hz), 7.71-7.75 (m, 2H), 7.56-7.66 (m, 2H), 7.36 (d, 1H, J=2.07 Hz), 7.22 (dd, 1H, J=9.15 Hz and 2.31 Hz), 4.30-4.33 (m, 2H), 4.05 (s, 3H), 3.33-3.34 (m, 2H), 2.99-3.05 (m, 2H), 1.19-1.23 ppm (m, 3H). Elemental Analysis for C22H23N3O3S.1.00 mol HCl.0.40 mol H2O: Calcd: C, 58.31; H, 5.52; N, 9.27; Found: C, 58.62; H, 5.54; N, 9.11.

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 20 minutes

Sources & evidence

ORD record
ord-3e1b51c114ac401b92bc0eabbbee6ba3
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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