Iodoethane → Ethanesulfonic acid {[5-(3-chloro-4-cyano-phenyl)-pyridin-3-yl]-cyclopropyl-methyl}-ethyl-amide

HRID 2407434ノート

反応式

HRID 2407434 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[C:12]([CH:16]([NH:20][S:21]([CH2:24][CH3:25])(=[O:23])=[O:22])[CH:17]3[CH2:19][CH2:18]3)[CH:13]=[N:14][CH:15]=2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[H-].[Na+].I[CH2:29][CH3:30]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[C:12]([CH:16]([N:20]([CH2:29][CH3:30])[S:21]([CH2:24][CH3:25])(=[O:23])=[O:22])[CH:17]3[CH2:19][CH2:18]3)[CH:13]=[N:14][CH:15]=2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

参加物

5

反応物 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 49819978N-((5-(3-chloro-4-cyanophenyl)pyridin-3-yl)(cyclopropyl)methyl)ethanesulfonamide

生成物 1

HCID 49820904Ethanesulfonic acid {[5-(3-chloro-4-cyano-phenyl)-pyridin-3-yl]-cyclopropyl-methyl}-ethyl-amide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

A 40 mL scintillation vial was charged with ethanesulfonic acid {[5-(3-chloro-4-cyano-phenyl)-pyridin-3-yl]-cyclopropyl-methyl}-amide (0.075 g, 0.200 mmol) and DMF (3 mL). The reaction mixture was cooled to 0° C. and sodium hydride (0.012 g, 0.299 mmol) was added. The reaction was left to stir at room temperature for 20 min followed by the addition of iodoethane (0.050 g, 0.319 mmol). The reaction was stirred at room temperature overnight. The reaction was quenched with water (0.5 mL) and filtered. The filtrate was dissolved in DMF (3 mL) and purified using Xbridge C18 eluting with a 10 to 100% ACN-water to afford pure product ethanesulfonic acid {[5-(3-chloro-4-cyano-phenyl)-pyridin-3-yl]-cyclopropyl-methyl}-ethyl-amide as a white color solid. HRMS: (ESI) m/z 404.1190 [(M+H)+ Calcd for C20H22ClN3O2S 404.1199]. 1H NMR (400 MHz, MeOD) δ ppm 0.52-0.68 (m, 1H), 0.71-0.82 (m, 1H), 0.91-1.05 (m, 2H), 1.22 (t, J=7.1 Hz, 3H), 1.43 (t, J=7.5 Hz, 3H), 1.60-1.88 (m, 1H), 3.28 (q, J=7.3 Hz, 2H), 3.39-3.51 (m, 1H), 3.55-3.66 (m, 1H), 4.32 (d, J=10.6 Hz, 1H), 7.93 (dd, J=8.1, 1.8 Hz, 1H), 8.06 (d, J=8.3 Hz, 1H), 8.15 (d, J=1.5 Hz, 1H), 8.87 (s, 1H), 9.04 (d, J=1.8 Hz, 1H), 9.14 (d, J=1.8 Hz, 1H).

後処理

  1. waitThe reaction was left
  2. stirringThe reaction was stirred at room temperature overnight
  3. customThe reaction was quenched with water (0.5 mL)
  4. filtrationfiltered
  5. dissolutionThe filtrate was dissolved in DMF (3 mL)
  6. custompurified
  7. washC18 eluting with a 10 to 100% ACN-water

出典と根拠

ORDレコード
ord-1483e49ced0a42f7885efdc9cadf228b
出典データセット
uspto-grants-2014_08
特許番号
US08809545B2

反応ノート

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