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

HRID 1777965Notes

Reaction equation

HRID 1777965 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-00483b89a7344602a1df823fcdb0219c
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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