Potassium Carbonate → HCID 30074581、化合物

HRID 243665

反応式

HRID 243665 の反応式
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].Br[C:10]1[S:11][C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cu](I)I>[S:11]1[C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=[C:10]1[N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 6120402-Bromo-1,3-benzothiazole

生成物 1

HCID 30074581HCID 30074581、化合物収率 60%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of 28 mg (0.24 mmol) of L-Proline in N,N-dimethylformamide (3 mL) at ambient temperature was added 51 mg (0.24 mmol) of 2-bromobenzothiazole, 100 mg (0.72 mmol) of potassium carbonate, and 6 mg (0.03 mmol) of copper iodide. The reaction mixture was stirred at 100° C. overnight. It was then filtered and purified by reverse-phase HPLC (TMC Pro-Pac C18; 0-60% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient). The pure fractions were lyophilized overnight to give 35 mg 60% of the title compound as a light brown solid. 1H NMR (DMSO-d6): δ 7.78 (d, J=8.0 Hz, 1H), 7.45 (d, J=8.0 Hz, 1H), 7.28 (t, J=7.8 Hz, 1H), 7.08 (t, J=7.8 Hz, 1H), 4.48 (d, J=7.3 Hz, 1H), 3.52-3.61 (m, 2H), 2.37 (m, 1H), 2.01-2.11 (m, 3H). LC/MS 249.3 (M+1)

後処理

  1. filtrationIt was then filtered
  2. custompurified by reverse-phase HPLC (TMC Pro-Pac C18; 0-60% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient)
  3. waitThe pure fractions were lyophilized overnight

出典と根拠

ORDレコード
ord-0b17337e941e467498412f509ef96dc1
出典データセット
uspto-grants-2014_02
特許番号
US08653260B2

関連ノート

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