Potassium Carbonate → 6-Bromo-2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)benzo[d]thiazole

HRID 1429522ノート

反応式

HRID 1429522 の反応式
[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([O:9][CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[S:8][C:4]=2[CH:3]=1.Cl[C:19]1[N:24]=[CH:23][C:22]([CH2:25][CH2:26][CH3:27])=[CH:21][N:20]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([O:9][CH:10]3[CH2:11][CH2:12][N:13]([C:19]4[N:24]=[CH:23][C:22]([CH2:25][CH2:26][CH3:27])=[CH:21][N:20]=4)[CH2:14][CH2:15]3)[S:8][C:4]=2[CH:3]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 27357842-Chloro-5-propylpyrimidineHCID 674668246-Bromo-2-(piperidin-4-yloxy)-benzothiazole

生成物 1

HCID 674627936-Bromo-2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)benzo[d]thiazole収率 50%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of 6-bromo-2-(piperidin-4-yloxy)benzo[d]thiazole (190 mg, 0.607 mmol) and 2-chloro-5-propylpyrimidine (114 mg, 0.728 mmol) in DMF (4 mL) was added K2CO3 (252 mg, 1.820 mmol). Upon completion of addition, the reaction mixture was heated to 100° C., where it stirred overnight. At the conclusion of this period, the reaction mixture was cooled to rt, diluted with water (10 mL) and then extracted with EtOAc (3×10 mL). The combined organic layers were dried (Na2SO4), filtered, and then concentrated to yield the crude product. The crude product was purified by column chromatography (silica gel, hexanes-EtOAc gradient 0 to 30% EtOAc) to afford Compound 1C as a white solid (131 mg, 0.302 mmol, 50% yield). 1H NMR (500 MHz, chloroform-d) δ ppm 8.17 (s, 2H), 7.77 (d, J=1.9 Hz, 1H), 7.51-7.56 (m, 1H), 7.44-7.49 (m, 1H), 5.40-5.49 (m, J=7.9, 7.9, 4.0, 3.9 Hz, 1H), 4.23 (ddd, J=13.4, 6.8, 4.0 Hz, 2H), 3.63-3.73 (m, 2H), 2.42 (t, J=7.6 Hz, 2H), 2.14-2.22 (m, 2H), 1.89-1.99 (m, 2H), 1.56-1.64 (m, 2H), 0.95 (t, J=7.4 Hz, 3H).

後処理

  1. additionUpon completion of addition
  2. temperatureAt the conclusion of this period, the reaction mixture was cooled to rt
  3. extractionextracted with EtOAc (3×10 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield the crude product
  8. customThe crude product was purified by column chromatography (silica gel, hexanes-EtOAc gradient 0 to 30% EtOAc)

出典と根拠

ORDレコード
ord-73b65d31a82044c2bc7b15fc5db34472
出典データセット
uspto-grants-2015_01
特許番号
US08940716B2

反応ノート

読み込み中…