Pyridine → Phenyl (5-cyano-4-(2-methoxyethoxy)pyridin-2-yl)carbamate

HRID 1777965노트

반응식

HRID 1777965 반응식
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[NH2:11][C:12]1[CH:19]=[C:18]([O:20][CH2:21][CH2:22][O:23][CH3:24])[C:15]([C:16]#[N:17])=[CH:14][N:13]=1.N1C=CC=CC=1>C1COCC1>[C:5]1([O:4][C:2](=[O:3])[NH:11][C:12]2[CH:19]=[C:18]([O:20][CH2:21][CH2:22][O:23][CH3:24])[C:15]([C:16]#[N:17])=[CH:14][N:13]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 1180368416-Amino-4-(2-methoxyethoxy)nicotinonitrile2회

생성물 1

HCID 125470569Phenyl (5-cyano-4-(2-methoxyethoxy)pyridin-2-yl)carbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Phenyl chloroformate (4.93 ml, 39.3 mmol) was added drop wise to a mixture of 6-amino-4-(2-methoxyethoxy)nicotinonitrile (intermediate 20, 3.45 g, 17.86 mmol) and pyridine (6.35 ml, 79 mmol) in THF (100 ml) at room temperature. The reaction mixture was stirred for 5 h at room temperature and then partitioned between EtOAc and saturated aqueous NaHCO3 solution, the organic layer washed with saturated brine, dried over MgSO4 and evaporated. The residue was triturated with EtOAc and the product obtained by filtration as a white solid. (UPLC-MS 7) tR 0.97; ESI-MS 314.3 [M+H]+.

후처리

  1. custompartitioned between EtOAc and saturated aqueous NaHCO3 solution
  2. washthe organic layer washed with saturated brine
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue was triturated with EtOAc
  6. customthe product obtained by filtration as a white solid

출처 및 근거

ORD 기록
ord-00483b89a7344602a1df823fcdb0219c
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266883B2

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