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

HRID 1777954Notes

Reaction equation

HRID 1777954 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][CH:21]([CH3:23])[CH3:22])[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][CH:21]([CH3:23])[CH3:22])[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 1049Pyridine2×HCID 15891Phenyl chloroformateHCID 1180369706-Amino-4-isopropoxynicotinonitrile2×

Product 1

HCID 125470513Phenyl (5-cyano-4-isopropoxypyridin-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyl chloroformate (3.89 ml, 31.0 mmol) was added drop wise to a mixture of 6-amino-4-isopropoxynicotinonitrile (intermediate 97, 2.5 g, 14.11 mmol) and pyridine (2.51 ml, 31.0 mmol) in THF (100 ml) at room temperature. The reaction mixture was stirred for 12 h at room temperature, additional pyridine (2.51 ml, 31.0 mmol) added, before stirring for an additional 12 h and then partitioned between EtOAc and saturated aqueous NaHCO3 solution. The organic layer was washed with saturated brine, dried over MgSO4 and evaporated. The residue was triturated with Et2O and the product obtained by filtration as a beige solid. (UPLC-MS 7) tR 1.09; ESI-MS 298.2 [M+H]+.

Workup

  1. stirringbefore stirring for an additional 12 h
  2. custompartitioned between EtOAc and saturated aqueous NaHCO3 solution
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was triturated with Et2O
  7. customthe product obtained by filtration as a beige solid

Sources & evidence

ORD record
ord-c00926421b5b44e0871bb723bb874072
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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