Diethylamine → HCID 16071254, compound

HRID 2240025Notes

Reaction equation

HRID 2240025 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][CH2:41][CH3:42])[CH3:39]>C1COCC1>[CH2:38]([N:40]([CH2:41][CH3:42])[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:33]2[C:32](=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:31]=[CH:30][CH:29]=1)(=[O:27])=[O:26])[CH3:39]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 58812060HCID 58812060, compound

Product 1

HCID 16071254HCID 16071254, compound

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 (0.385 g, 0.717 mmol) and diethylamine (2.0 mL, 19 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 chloroform 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 diethyl-{2-[1-methyl-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl}-amine a clear amber gum (0.269 g, 85.7%). 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 brown foam (0.253 g); Mass Spectrum (+EI, [M+H]+) m/z 438. 1HNMR (500 MHz, DMSO-d6): δ10.11-10.12 (br, 1H), 8.74 (d, 1H, J=8.66 Hz), 8.50-8.52 (m, 1H), 8.27 (d, 1H, J=8.29 Hz), 8.03-8.05 (m, 1H), 7.71-7.75 (m, 2H), 7.56-7.66 (m, 2H), 7.37 (d, 1H, J=2.20 Hz), 7.21 (dd, 1H, J=9.27 Hz and 2.32 Hz), 4.41-4.43 (m, 2H), 4.05 (s, 3H), 3.49-3.52 (m, 2H), 3.15-3.25 (m, 4H), 1.22-1.25 ppm (m, 6H).

Workup

  1. customevaporated
  2. customThe residue was partitioned in chloroform
  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-a711d24196fe4dc6a0cdd7102e267ca3
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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