Methylamine → {2-[1-benzyl-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl}-methyl-amine

HRID 2240030Notes

Reaction equation

HRID 2240030 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19]OS(C3C=CC(C)=CC=3)(=O)=O)=[CH:14][CH:15]=2)[C:10]([S:31]([C:34]2[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH:37]=[CH:36][CH:35]=2)(=[O:33])=[O:32])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.[CH3:49][NH2:50]>>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][NH:50][CH3:49])=[CH:14][CH:15]=2)[C:10]([S:31]([C:34]2[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH:37]=[CH:36][CH:35]=2)(=[O:33])=[O:32])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 58812069toluene-4-sulfonic acid 2-[1-benzyl-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl ester

Product 1

HCID 16070640{2-[1-benzyl-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl}-methyl-amine

Procedure

A solution of toluene-4-sulfonic acid 2-[1-benzyl-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl ester (0.476 g, 0.777 mmol) in 2.0 M methylamine in THF (8.0 mL, 16 mmol) was stirred at 70° C. in a sealed tube for 3 hours. After cooling to ambient temperature and concentrating, the residue was partitioned in ethyl acetate and aqueous sodium bicarbonate. The organic phase was washed with water and brine. It was dried with anhydrous magnesium sulfate, filtered and concentrated. Drying at 80° C. in vacuo for 20 minutes gave {2-[1-benzyl-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl}-methyl-amine as a clear, dark yellow gum (0.324 g, 88.5%). This was dissolved in chloroform, and ethereal hydrochloride was added. The mixture was concentrated and dried at 81° C. in vacuo for 13 hours. The hydrochloride as a light orange foam (0.330 g) resulted; Mass Spectrum (+EI, [M+H]+) m/z 472. 1HNMR (500 MHz, DMSO-d6): δ8.86 (s, 2H), 8.74-8.77 (m, 1H), 8.54-8.56 (m, 1H), 8.27 (d, 1H, J=8.30 Hz), 8.02-8.05 (m, 1H), 7.79 (d, 1H, J=9.15 Hz), 7.70-7.74 (m, 1H), 7.58-7.65 (m, 2H), 7.27 (d, 1H, J=3.30 Hz), 7.09-7.18 (m, 6H), 5.70 (s, 2H), 4.24-4.27 (m, 2H), 2.59 ppm (s, 3H). Elemental Analysis for C27H25N3O3S2.1.00 HCl.0.55 mol H2O: Calcd: C, 62.61; H, 5.27; N, 8.11; Found: C, 62.23; H, 5.45; N, 7.72.

Workup

  1. concentrationconcentrating
  2. customthe residue was partitioned in ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialIt was dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customDrying at 80° C. in vacuo for 20 minutes

Sources & evidence

ORD record
ord-11c564f33e2d475aad67d61b55cb07f9
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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