反応 #58434

反応方程式

[4-Amino-2-(piperidin-4-ylamino)thiazol-5-yl]-(3-fluorophenyl)methanone

[4-amino-2-(piperidin-4-ylamino)thiazol-5-yl]-(3-fluorophenyl)methanone

acetyl chloride

→

1-[4-[4-amino-5-(3-fluorobenzoyl)thiazol-2-ylamino]piperidin-1-yl]ethanone

収率 31.2%

溶媒

tetrahydrofuran

chloroform

pyridine

methylene chloride

反応条件

後処理

1. 1
   その他at room temperature
2. 2
   洗浄washed with 10% Na2CO3(aq) (2×)
3. 3
   その他After drying
4. 4
   その他(Na2SO4) and solvent removal
5. 5
   その他the residue was precipitated from a mixture of tetrahydrofuran and hexane

実験手順

[4-Amino-2-(piperidin-4-ylamino)thiazol-5-yl]-(3-fluorophenyl)methanone (0.10 g, 0.31 mmol) (Example 6) was dissolved in a mixture of tetrahydrofuran (20 mL), chloroform (6 mL), and pyridine and cooled to −10° C. This was treated with acetyl chloride (0.032 g, 43 mmol) and stirred for 0.5 hr. at room temperature. This was diluted with cold methylene chloride (100 mL) and washed with 10% Na2CO3(aq) (2×). After drying (Na2SO4) and solvent removal, the residue was precipitated from a mixture of tetrahydrofuran and hexane to give 35 mg (30% yield) of 1-[4-[4-amino-5-(3-fluorobenzoyl)thiazol-2-ylamino]piperidin-1-yl]ethanone. 1H NMR (DMSO−d6, 300 MHz) δ1.28 (m, 1H, CH), 1.41 (m, 1H, CH) 1.92 (m, 2H, CH2), 2.75 (t, 1H, NCH), 3.14 (t, H, NCH), 3.32 (s, 3H, COCH3), 3.6-4.0 (broad, 1H, CH), 3.77 (d, 1H, NCH), 4.22 (d, 1H, NCH), 7.31 (t, 1H, Aromatic), 7.38 (d, 1H, Aromatic), 7.48 (t, 1H, Aromatic), 7.51 (q, 1H, Aromatic), 8.01 (brd, 1H, NH), 8.48 (brd, 1H, NH), 8.72 (brd, 1H, NH). HRMS: (M+H)+: observed: 363.1288; calcd for 363.1286.

出典