Diethylamine → HCID 178463999, compound

HRID 2240008Notes

Reaction equation

HRID 2240008 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]2C(=CC=[CH:8][CH:9]=2)C=[CH:3][CH:2]=1.[CH2:38]([NH:40][CH2:41][CH3:42])[CH3:39].[CH2:43]1[CH2:47]O[CH2:45][CH2:44]1>>[CH2:38]([N:40]([CH2:41][CH3:42])[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:9](=[CH:47][CH:43]=[CH:44][CH:45]=2)[CH:8]=[CH:3][CH:2]=1)(=[O:13])=[O:12])[CH3:39]

Participants

4

Reactant 3

HCID 8021DiethylamineHCID 8028TetrahydrofuranHCID 178427737HCID 178427737, compound

Product 1

HCID 178463999HCID 178463999, 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 diethylamine (0.45-0.75 mmol) in THF (10 mL) 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 chloroform, and ethereal hydrochloride was added. The mixture was concentrated and dried in vacuo at 80° C. for 17 hours. Diethyl-{3-[3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-propyl}-amine hydrochloride was a tan foam (69.9 mg, 98.3%); Mass Spectrum (+EI, [M+H]+) m/z 438. 1HNMR (500 MHz, DMSO-d6): δ14.13-14.11 (br, 1H), 9.59-9.63 (br, 1H), 8.75 (d, 1H, J=8.42 Hz), 8.51 (dd, 1H, J=7.44 Hz and 1.10 Hz), 8.27 (d, 1H, J=8.29 Hz), 8.03-8.05 (m, 1H), 7.70-7.74 (m, 1H), 7.52-7.64 (m, 3H), 7.05-7.11 (m, 2H), 4.10 (t, 2H, J=5.98 Hz), 3.11-3.25 (m, 6H), 2.09-2.24 (m, 2H), 1.18 ppm (t, 6H, J=7.20 Hz).

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. additionchloroform, and ethereal hydrochloride was added
  9. concentrationThe mixture was concentrated
  10. customdried in vacuo at 80° C. for 17 hours

Sources & evidence

ORD record
ord-d61e03937e7e4b918d357636582b73ac
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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