Ethylamine tetrahydrofuran → HCID 178464184, compound

HRID 2240006Notes

Reaction equation

HRID 2240006 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.[CH2:38]([NH2:40])[CH3:39].C1COCC1>>[CH2:38]([NH:40][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])[CH3:39]

Participants

3

Reactant 2

HCID 66726184Ethylamine tetrahydrofuranHCID 178427737HCID 178427737, compound

Product 1

HCID 178464184HCID 178464184, compoundYield 70%

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) in 10 mL of 2.0 M ethylamine/THF (20 mmoles) 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 purified by flash chromatography using 0.75% ammonium hydroxide/7.5% methanol in chloroform. Drying at 66° C. in vacuo for 20 minutes yielded ethyl-{3-[3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-propyl}-amine as a light yellow foam (43.0 mg, 70.0%). This was dissolved in methanol and ethereal hydrochloride was added. Concentrating and drying in vacuo at 83° C. for 16 hours gave the hydrochloride as a pale yellow semi-solid (41.7 mg, 62.3%). Mass Spectrum (+EI, [M+H]+) m/z 410; 1HNMR (500 MHz, DMSO-d6): δ14.14-14.18 (br, 1H), 8.74-8.76 (m, 1H), 8.56-8.72 (br, 2H), 8.52 (dd, 1 h, J=7.44 Hz and 1.22 Hz), 8.27 (d, 1H, J=8.29 Hz), 8.03-8.05 (m, 1H), 7.71-7.75 (m, 1H), 7.54-7.65 (m, 3H), 7.29 (d, 1H, J=2.08 Hz), 7.07-7.10 (m, 1H), 4.09-4.12 (m, 2H), 3.03-3.07 (m, 2H), 2.90-2.97 (m, 2H), 2.05-2.12 (m, 2H), 1.15-1.19 ppm (m, 3H). Elemental Analysis for C22H23N3O3S.1.00 mol HCl.1.20 mol H2O: Calcd: C, 56.51; H, 5.69; N, 8.99; Found: C, 56.20; H, 5.36; N, 8.81.

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. customThe residue was purified by flash chromatography
  8. customDrying at 66° C. in vacuo for 20 minutes

Sources & evidence

ORD record
ord-2946e0cbdfcc4cec8f10b8a80d936eea
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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