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

HRID 1777965ノート

反応式

HRID 1777965 の反応式
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

参加物

5

反応物 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 1180368416-Amino-4-(2-methoxyethoxy)nicotinonitrile2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-00483b89a7344602a1df823fcdb0219c
出典データセット
uspto-grants-2016_02
特許番号
US09266883B2

反応ノート

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