Hydrochloric Acid → HCID 16071026, compound

HRID 2240040Notes

Reaction equation

HRID 2240040 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:42]=[CH:43][CH:44]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][CH2:17]OS(C3C=CC(C)=CC=3)(=O)=O)=[CH:12][CH:13]=2)[C:8]([S:29]([C:32]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:35]=[CH:34][CH:33]=2)(=[O:31])=[O:30])=[N:7]1.C1COCC1.Cl.[CH2:51]([NH2:53])[CH3:52]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:42]=[CH:43][CH:44]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][CH2:17][NH:53][CH2:51][CH3:52])=[CH:12][CH:13]=2)[C:8]([S:29]([C:32]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:35]=[CH:34][CH:33]=2)(=[O:31])=[O:30])=[N:7]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6341EthylamineHCID 8028TetrahydrofuranHCID 58812063toluene-4-sulfonic acid 2-[1-(3-chloro-benzyl)-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl ester

Product 1

HCID 16071026HCID 16071026, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of toluene-4-sulfonic acid 2-[1-(3-chloro-benzyl)-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl ester (0.415 g, 0.641 mmol) in 2.0 M ethylamine in THF (8.0 mL, 16.0 mmol) was stirred at 70° C. for 3 hours and then at 80° C. for 19 hours. The reaction mixture was allowed to cool to ambient temperature and solvent evaporated. It was partitioned in ethyl acetate and aqueous sodium bicarbonate. The organic phase was washed with brine, dried with magnesium sulfate, filtered and concentrated. Drying in vacuo at 80° C. for 20 minutes resulted in {2-[1-(3-chloro-benzyl)-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl}-ethyl-amine as an orange semi-solid (0.270 g, 81.1%). This was dissolved in chloroform, and ethereal hydrochloride was added. The mixture was concentrated and dried in vacuo at 83° C. for 16 hours. The hydrochloride as a pale orange foam resulted (0.276 g); Mass Spectrum (+EI, [M+H]+) m/z 520. 1HNMR (500 MHz, DMSO-d6): δ8.71-8.77 (m, 3H), 8.55 (dd, 1H, J=7.44 Hz and 1.22 Hz), 8.27 (d, 1H, J=8.29 Hz), 8.02-8.05 (m, 1H), 7.82 (d, 1H, J=9.15 Hz), 7.70-7.74 (m, 1H), 7.57-7.64 (m, 2H), 7.24-7.28 (m, 2H), 7.16-7.21 (m, 3H) 7.05 (d, 1H, J=7.56 Hz), 5.73 (s, 2H), 4.24-4.27 (m, 2H), 3.30-3.32 (m, 2H), 2.97-3.03 (m, 2H), 1.16-1.20 ppm (m, 3H). Elemental Analysis for C28H26ClN3O3S.1.00 HCl.0.60 mole H2O: Calcd: C, 59.28; H, 5.01; N, 7.41; Found: C, 58.95; H, 5.06; N, 7.14.

Workup

  1. customsolvent evaporated
  2. customIt was partitioned in ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customDrying in vacuo at 80° C. for 20 minutes
  8. customresulted in {2-[1-(3-chloro-benzyl)-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl}-ethyl-amine as an orange semi-solid (0.270 g, 81.1%)
  9. concentrationThe mixture was concentrated
  10. customdried in vacuo at 83° C. for 16 hours

Sources & evidence

ORD record
ord-e391511ebe5e42dc9a2cb2967ba002d4
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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