Hydrochloric Acid → HCID 178464069, compound

HRID 2240007Notes

Reaction equation

HRID 2240007 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][CH2:26]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.[CH3:38][NH:39][CH2:40][CH3:41].Cl.O>>[CH2:40]([N:39]([CH3:38])[CH2:26][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])[CH3:41]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 12219N-MethylethylamineHCID 178427737HCID 178427737, compound

Product 1

HCID 178464069HCID 178464069, compound

Procedure

A solution of toluene-4-sulfonic acid 3-[3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-propyl ester (0.080 mg, 0.15 mmol) and methyethylamine (0.45-0.75 mmol) was stirred at 90° C. for about 2 hours in a sealed tube. After cooling to ambient temperature the reaction mixture was solvent evaporated. It was dissolved in ethyl acetate and washed twice with aqueous sodium bicarbonate. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was dissolved in methanol, and ethereal hydrochloride was added. The mixture was then concentrated and dried for 29 hours at 80° C. in vacuo. Ethyl-methyl-{3-[3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-propyl}-amine hydrochloride was a tan semi-solid (53.2 mg, 77.1%); Mass Spectrum (+EI, [M+H]+) m/z 424. 1HNMR (500 MHz, DMSO-d6): δ14.14-14.17 (br, 1H), 9.71-9.77 (br, 1H), 8.74-8.76 (m, 1H), 8.52 (dd, 1H, J=7.44 Hz and 1.22 Hz), 8.27 (d, 1H, J=8.30 Hz), 8.03-8.05 (m, 1H), 7.70-7.74 (m, 1H), 7.56-7.64 (m, 3H), 7.29 (d, 1H, J=2.19 Hz), 7.08-7.10 (m, 1H), 4.08-4.11 (m, 2H), 3.04-3.25 (m, 2H), 2.72 (s, 3H), 1.18-1.21 ppm (m, 3H). Elemental Analysis for C23H25N3O3S. 1.00 mol HCl.0.90 mol H2O: Calcd: C, 58.01; H, 5.88; N, 8.82; Found: C, 58.37; H, 5.55; N, 8.50.

Workup

  1. customevaporated
  2. dissolutionIt was dissolved in ethyl acetate
  3. washwashed twice with aqueous sodium bicarbonate
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in methanol
  8. additionethereal hydrochloride was added
  9. concentrationThe mixture was then concentrated
  10. customdried for 29 hours at 80° C. in vacuo

Sources & evidence

ORD record
ord-9f44067c21d6461d82f56ad97d720877
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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