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

HRID 1864663노트

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HRID 1864663 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-fce6cf9ca5a341f5a425f32e1ef35149
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07625922B2

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