N-Methylethylamine → HCID 16071143, compound

HRID 2240024Notes

Reaction equation

HRID 2240024 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]([NH:40][CH3:41])[CH3:39]>C1COCC1>[CH2:38]([N:40]([CH3:41])[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 12219N-MethylethylamineHCID 58812060HCID 58812060, compound

Product 1

HCID 16071143HCID 16071143, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of toluene-4-sulfonic acid 2-[1-methyl-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl ester (0.398 g, 0.742 mmol) and ethylmethylamine (2.0 mL, 23 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-methyl-{2-[1-methyl-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl}-amine as a light brown gum (0.227 g, 72.3%). This was dissolved in chloroform, and etheric 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 424. 1HNMR (500 MHz, DMSO-d6): δ10.26-10.27 (s, br, 1H), 8.75 (d, 1H, J=8.66 Hz), 8.50-8.53 (m, 1H), 8.27 (d, 1H, J=8.17 Hz), 8.04 (d, 1H, J=7.56 Hz), 7.71-7.75 (m, 2H), 7.56-7.66 (m, 2H), 7.38 (d, 1H, J=2.19 H) 7.22 (dd, 1H, J=9.15 Hz and 2.32 Hz), 4.43 (t, 2H, J=4.88 Hz), 4.05 (s, 3H), 3.40-3.60 (m, 3H), 3.10-3.20 (br, 1H), 2.80 (s, 3H), 1.22-1.26 ppm (m, 3H).

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-fd4ab67ef15142cf8dacfcc36736d74d
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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