Tetrahydrofuran → {2-[1-Benzyl-3-(naphthalene-1-sulfonyl)-1h-indazol-5-yloxy]-ethyl}-ethyl-methyl-amine

HRID 2240029ノート

反応式

HRID 2240029 の反応式
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12]C(OCCOS(C3C=CC(C)=CC=3)(=O)=O)=C[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.[CH2:44]([NH:46][CH3:47])[CH3:45].[CH2:48]1[CH2:52][O:51][CH2:50][CH2:49]1>>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:50]([O:51][CH2:52][CH2:48][N:46]([CH2:44][CH3:45])[CH3:47])=[CH:49][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:32])=[O:33])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 3

HCID 8028TetrahydrofuranHCID 12219N-MethylethylamineHCID 58812069toluene-4-sulfonic acid 2-[1-benzyl-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl ester

生成物 1

HCID 58812097{2-[1-Benzyl-3-(naphthalene-1-sulfonyl)-1h-indazol-5-yloxy]-ethyl}-ethyl-methyl-amine収率 81.4%

実験手順

A solution of toluene-4-sulfonic acid 2-[1-benzyl-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl ester (0.363 g, 0.592 mmol) and ethylmethylamine (2.0 mL, 23 mmol) in THF (8 mL) was stirred at 70° C. for 2.5 hours in a sealed tube. After cooling to ambient temperature, the residue was partitioned in ethyl acetate and aqueous sodium bicarbonate. The organic phase was washed with brine, dried with anhydrous magnesium sulfate, filtered and concentrated. Drying at 80° C. in vacuo for 30 minutes gave {2-[1-benzyl-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl}-ethyl-methyl-amine as a yellow foam/gum (0.241 g, 81.4%). This was dissolved in chloroform, and ethereal hydrochloride was added. The mixture was concentrated and dried in vacuo for 13 hours to yield the hydrochloride as a buff foam (0.242 g). Mass Spectrum (+EI, [M+H]+) m/z 500. 1HNMR (500 MHz, DMSO-d6): δ10.04-10.10 (s, br, 1H), 8.74-8.77 (m, 1H), 8.54-8.56 (m, 1H), 8.27 (d, 1H, J=8.29 Hz), 8.02-8.05 (m, 1H), 7.79 (d, 1H, J=9.28 Hz), 7.70-7.74 (m, 1H), 7.55-7.67 (m, 2H), 7.28 (d, 1H, J=2.19 Hz), 7.04-7.20 (m, 6H), 5.70 (s, 2H), 4.35 (s, 2H), 3.33-3.41 (br, 2H), 3.01-3.19 (br, 2H), 2.73 (s, 3H), 1.17-1.21 ppm (m, 3H). Elemental Analysis for C29H29N3O3S.1.00 mol HCl.1.10 mol H2O: Calcd: C, 62.66; H, 5.84; N, 7.56; Found: C, 62.73; H, 6.19; N, 7.17.

後処理

  1. customthe residue was partitioned in ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customDrying at 80° C. in vacuo for 30 minutes

出典と根拠

ORDレコード
ord-d8db7c5ad6a44404acd0055191a40041
出典データセット
uspto-grants-2010_05
特許番号
US07723329B2

反応ノート

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