Propionyl chloride → Methyl 3-amino-6-(1-propanoyl-4-piperidyl)pyrazine-2-carboxylate

HRID 1959477Notes

Reaction equation

HRID 1959477 reaction equation
[NH2:1][C:2]1[C:3]([C:14]([O:16][CH3:17])=[O:15])=[N:4][C:5]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:6][N:7]=1.[C:18](Cl)(=[O:21])[CH2:19][CH3:20]>C(=O)(O)[O-].[Na+].ClCCl>[NH2:1][C:2]1[C:3]([C:14]([O:16][CH3:17])=[O:15])=[N:4][C:5]([CH:8]2[CH2:9][CH2:10][N:11]([C:18](=[O:21])[CH2:19][CH3:20])[CH2:12][CH2:13]2)=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 62324Propionyl chlorideHCID 66744323Methyl 3-amino-6-(4-piperidyl)pyrazine-2-carboxylate

Product 1

HCID 66745330Methyl 3-amino-6-(1-propanoyl-4-piperidyl)pyrazine-2-carboxylateYield 66.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a rapidly stirring biphasic solution of methyl 3-amino-6-(4-piperidyl)pyrazine-2-carboxylate (135 mg, 0.57 mmol) in 50% saturated sodium bicarbonate and dichloromethane (20 mL) at 25° C. was added propanoyl chloride (79 mg, 75 μL, 0.86 mmol) dropwise. The reaction was stirred at room temperature for 30 minutes. The organic layer was separated, dried over Na2SO4, filtered, and concentrated in vacuo to provide methyl 3-amino-6-(1-propionylpiperidin-4-yl)pyrazine-2-carboxylate (111 mg, 66%). 1H NMR (400 MHz, DMSO-d6) δ 8.25 (s, 1H), 7.19 (s, 2H), 4.51 (d, J=12.9 Hz, 1H), 3.95 (d, J=13.6 Hz, 1H), 3.84 (s, 3H), 3.08 (t, J=12.2 Hz, 1H), 2.88 (ddd, J=15.5, 7.9, 3.7 Hz, 1H), 2.61 (t, J=11.7 Hz, 1H), 2.34 (q, J=7.5 Hz, 2H), 1.80 (t, J=13.7 Hz, 2H), 1.69-1.39 (m, 2H), 1.00 (t, J=7.4 Hz, 3H). LC/MS m/z 293.5 [M+H]

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b06ed0c79d77451382475d22c1067b0b
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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