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

HRID 2272678노트

반응식

HRID 2272678 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][C:3]=1[F:22].[H-].[Na+].[CH3:25]I>C1COCC1>[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[N:14]([CH3:25])[C:15](=[O:19])[O:16][CH2:17][CH3:18])=[CH:4][C:3]=1[F:22]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 44184952HCID 44184952, 화합물

생성물 1

HCID 44184953Ethyl 4-(4-amino-3-fluorophenoxy)-2-aminopyridin-3-yl-methyl-carbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

Ethyl 4-(4-amino-3-fluorophenoxy)-2-aminopyridin-3-yl-carbamate (6a) (480 mg, 1.6 mmol) was dissolved in dry THF (8 mL) and cooled at 0° C. Sodium hydride (60% in mineral oil, 80 mg, 2.0 mmol) was added, and the reaction mixture was stirred for 40 minutes at 0° C. Methyl iodide (130 μL, 1.8 mmol) was added at 0° C. The ice bath was removed, and the mixture was stirred at room temperature for 18 hours. The solvent was evaporated and the residue partitioned between DCM and distilled water. The organic layer was dried and evaporated, and the residue washed with diethyl ether to afford the title compound as a brown solid.

후처리

  1. customThe ice bath was removed
  2. stirringthe mixture was stirred at room temperature for 18 hours
  3. customThe solvent was evaporated
  4. customthe residue partitioned between DCM
  5. distillationdistilled water
  6. customThe organic layer was dried
  7. customevaporated
  8. washthe residue washed with diethyl ether

출처 및 근거

ORD 기록
ord-4c39f5d9f96943498afaf75ed55f763b
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120789B2

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