Hydrochloric Acid → Octanedioic acid hydroxyamide [4-(2-amino-phenyl)-thiazol-2-yl]-amide

HRID 243622

反応式

HRID 243622 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:11]=[C:12]([NH:15][C:16](=[O:34])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH:25][O:26]CC2C=CC=CC=2)=[O:24])[S:13][CH:14]=1)([O-])=O.Cl.Cl[Sn]Cl.[OH-].[Na+]>CO.O>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:11]=[C:12]([NH:15][C:16](=[O:34])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH:25][OH:26])=[O:24])[S:13][CH:14]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 89972899Octanedioic acid benzyloxy-amide [4-(2-nitro-phenyl)-thiazol-2-yl]-amide

生成物 1

HCID 25032253Octanedioic acid hydroxyamide [4-(2-amino-phenyl)-thiazol-2-yl]-amide収率 53.2%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

To a mixture of compound 15 (0.040 g, 0.083 mmol) in methanol (2 ml) was added 1 ml of concentrated HCl. The suspension was cooled to 0° C. Then SnCl2 (0.094 g, 0.49 mmol) was added and the reaction mixture was stirred overnight at room temperature. The mixture was then diluted with 5 ml of water, adjusted to pH 10 with 5N NaOH and extracted with ethyl acetate (10 mL×3). The combined organic layers were washed with water, dried over K2CO3 and concentrated in vacuo. The crude product was purified by reverse phase HPLC to afford Octanedioic acid hydroxyamide [4-(2-amino-phenyl)-thiazol-2-yl]-amide 16 (0.016 g, 53% yield). NMR (400 MHz, DMSO-d6 cont 5% TFA) δ (ppm) 12.13 (1H, s), 7.56 (1H, d, J=7.0 Hz), 7.40 (1H, s), 7.09 (1H, t, J=7.0 Hz), 6.83 (1H, d, J=7.0 Hz), 6.72 (1H, m), 3.75-3.39 (4H, brs), 2.44 (2H, t, J=7.3 Hz), 2.29 (2H, t, J=7.3), 1.61 (2H, m), 1.51 (2H, m), 1.30 (4H, m).

後処理

  1. extractionextracted with ethyl acetate (10 mL×3)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over K2CO3
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by reverse phase HPLC

出典と根拠

ORDレコード
ord-32b3aa34c9f442b7a2bcada762483e2d
出典データセット
uspto-grants-2014_02
特許番号
US08653278B2

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