Methyl iodide → Ethyl 4-(4-aminophenoxy)-2-aminopyridin-3-yl-methyl-carbamate

HRID 1864663ノート

反応式

HRID 1864663 の反応式
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[C:8]=2[NH:14][C:15](=[O:19])[O:16][CH2:17][CH3:18])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:24]I>C1COCC1>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[C:8]=2[N:14]([CH3:24])[C:15](=[O:19])[O:16][CH2:17][CH3:18])=[CH:20][CH:21]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 42626049Ethyl 4-(4-aminophenoxy)-2-aminopyridin-3-yl-carbamate

生成物 1

HCID 42625502Ethyl 4-(4-aminophenoxy)-2-aminopyridin-3-yl-methyl-carbamate収率 53%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Method O1. Ethyl 4-(4-aminophenoxy)-2-aminopyridin-3-yl-carbamate (72 mg, 0.25 mmol) was dissolved in dry THF (3 mL) and cooled at 0° C. Sodium hydride (11 mg, 0.28 mmol) was added, and the reaction mixture was stirred for 25 minutes. Methyl iodide (18 μL, 0.25 mmol) was added. The mixture was stirred at 0° C. for 30 minutes and at room temperature for 1.5 hours. The solvent was evaporated and the residue extracted between DCM and saturated Na2CO3. The organic layer was dried and evaporated, and the residue purified by column chromatography (eluent AcOEt) to afford the title compound (40 mg, 53%). 1H-NMR (δ, ppm, DMSO-d6): 1.10 (t, 3H, CH3,Et, J=7.04 Hz), 3.01 (s, 3H, CH3N), 3.90-4.10 (m, 2H, CH2,Et), 5.06 (s, 2H, NH2,Ph), 5.78 (d, 1H, HPy,5, J=6.68 Hz), 5.97 (s, 2H, NH2,Py2), 6.59 (d, 2H, Harom,Ph,3+5, J=8.76 Hz), 6.73 (d, 2H, Harom,Ph,2+6, J=8.79 Hz), 7.67 (d, 1H, HPy,6, J=5.73 Hz). LC-MS (m/z): 302 (M+, 100). Acc. mass (C15H19N4O3): calculated 303.1457, found 303.1453.

後処理

  1. stirringThe mixture was stirred at 0° C. for 30 minutes and at room temperature for 1.5 hours
  2. customThe solvent was evaporated
  3. extractionthe residue extracted between DCM and saturated Na2CO3
  4. customThe organic layer was dried
  5. customevaporated
  6. customthe residue purified by column chromatography (eluent AcOEt)

出典と根拠

ORDレコード
ord-fce6cf9ca5a341f5a425f32e1ef35149
出典データセット
uspto-grants-2009_12
特許番号
US07625922B2

反応ノート

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