Potassium Carbonate → N-(5-Ethynylbicyclo[3.2.1]octan-1-yl)pyrazine-2-carboxamide

HRID 1503252Notes

Reaction equation

HRID 1503252 reaction equation
[CH:1]([C:3]12[CH2:10][C:7]([NH:11][C:12]([C:14]3[CH:19]=[N:18][CH:17]=[CH:16][N:15]=3)=[O:13])([CH2:8][CH2:9]1)[CH2:6][CH2:5][CH2:4]2)=O.[C:20]([O-])([O-])=O.[K+].[K+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-]>CO>[C:1]([C:3]12[CH2:10][C:7]([NH:11][C:12]([C:14]3[CH:19]=[N:18][CH:17]=[CH:16][N:15]=3)=[O:13])([CH2:8][CH2:9]1)[CH2:6][CH2:5][CH2:4]2)#[CH:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 117702640N-(5-Formylbicyclo[3.2.1]octan-1-yl)pyrazine-2-carboxamideHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 117702563N-(5-Ethynylbicyclo[3.2.1]octan-1-yl)pyrazine-2-carboxamideYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred mixture of N-(5-formylbicyclo[3.2.1]octan-1-yl)pyrazine-2-carboxamide (350 mg, 1.35 mmol) and K2CO3 (370 mg, 2.7 mmol) in methanol (25 mL) under N2 was added dimethyl (1-diazo-2-oxopropyl)phosphonate (310 mg, 1.62 mmol). After stirring at room temperature for three hours, the clear reaction solution was partitioned between ethyl acetate (20 mL) and 5% NaHCO3 (20 mL). The aqueous layer was extracted with ethyl acetate (2×20 mL). The combined organic phase was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford 210 mg (61%) of crude title compound, N-(5-ethynylbicyclo[3.2.1]octan-1-yl)pyrazine-2-carboxamide, as an off-white solid. ESI-MS m/z: 256 (M+H)+. It was used in the next step without further purification.

Workup

  1. customthe clear reaction solution was partitioned between ethyl acetate (20 mL) and 5% NaHCO3 (20 mL)
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×20 mL)
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3a753b68bf86436b997df366044e309b
Source dataset
uspto-grants-2015_12
Patent number
US09212165B2

Reaction notes

Loading…